


as if you don't remember (as if you can forget)

by alexisbldels



Category: Gilmore Girls
Genre: Canon Compliant, F/M, Fix It Fic, asp is busy so i guess i'll take it from here, takes place right after the Last Four Words(tm)
Language: English
Status: Completed
Published: 2019-08-31
Updated: 2020-03-08
Packaged: 2020-10-04 08:03:39
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 30
Words: 104,317
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20467736
Author URL: https://archiveofourown.org/users/alexisbldels/pseuds/alexisbldels
Summary: Jess Mariano has learned three things about love during his thirty-three years on earth. One: it never turns out the way you expect. Two: it never ends the way you want it to. Three: it always finds you in the strangest places.Or, Jess keeps putting off his return to Philly and Rory keeps running from her responsibilities, both set on rebuilding their friendship and hoping that their feelings go away. Post-AYITL.





	1. Prologue

**Author's Note:**

> Other characters/pairings: Lorelai, Luke, Paris, Emily, Lane, Logan, Chris, Matthew. Luke/Lorelai.  
Notes/Warnings: Post-AYITL. Canon compliant. Some sexual references.  
Disclaimer: The title is taken from the song "Silhouette" by Aquilo.

Jess Mariano has learned three things about love during his thirty-three years on earth. One: it never turns out the way you expect. Two: it never ends the way you want it to. Three: it always finds you in the strangest places.

Thirteen years ago, Jess was stuck in a hell of a town in Connecticut with no way out. But then he’d met a girl -- a girl who whenever she was around made all his sad stories into happy ones. And even though she wasn’t his, he loved her. He knew he loved her from the moment she first kissed him all those years ago -- even if that love had been there long before he knew. 

And then, the girl fell in love with him. They found the words only when the timing wasn’t right, when she was with someone else or he was gone or she was missing but in a different way than him. 

And even through all that, whenever they met again, they were always each other’s anchor, moral compass, inspiration -- no matter what. What stability they lacked in other relationships, they always found in each other. The feeling of dependence scared him every time. 

Then, he finds himself back in Stars Hollow, back in the town where he’d lost himself and found himself again -- and lost her for what he knows is forever. 

And now, he finds himself at her window once again, biting back the words he’d always been so petrified of. Because of course he still loves her -- _of course he does_. After everything they’ve faced, everything they’ve survived...how could he not?

  
  



	2. You'll Have to Swing It

**Summary for the Chapter:**

> Luke and Lorelai get married (again), but Rory can't stop thinking about Jess. But she's over him, right? Right?

**Notes for the Chapter:**

> from here on out updates won't be consistent, but i promise i won't disappear i p r o m i s e

“I’m pregnant.”   
Rory’s words hang in mid-air, followed by an uneasy silence. Her mother stares at her in shock, silent. For maybe the first time in her life, Lorelai Gilmore is speechless. 

Rory takes a shaky breath, trying to ignore the sinking feeling in her stomach. “Yeah,” she confirms. “Pregnant.” 

Lorelai blinks a few times, and suddenly, Rory feels exactly the same way she did when she was staring at the test. She can only imagine what comes next, what her mother might be thinking -- how could Rory Gilmore, the golden girl, be following in her footsteps? Getting knocked up unexpectedly and unprepared had always been something Rory was raised to avoid -- but here she is, sitting on the steps of the gazebo, admitting to the mistake of all mistakes. She’s scared Lorelai might be angry, sure, but what she’s terrified of the most is disappointment. She’s never handled that well, especially from her mom. 

The lack of a reaction only increases Rory’s anxiety, and she turns her phone over and over in her hands, wishing her mom would just say something _ . _

Finally, Lorelai breaks the silence. If she feels disappointed in any way, she doesn’t let on. “So, uh...are we happy about this, or do I need to get a  _ The Notebook _ volume of tissues?”

“I don’t know. I just…” Rory trails off, and she means it. How is she  _ supposed _ to feel? “It’s...unexpected.”

Lorelai nods solemnly, but doesn’t say anything. Rory doesn’t like the silence. She needs to fill it with  _ something _ .

“Really? No joke or witty comment to lighten the mood?” Rory inquires, half laughing, but it’s not because anything is funny.

The corners of Lorelai’s mouth turn upwards in a bittersweet smile. “Not this time, hon.” 

“Yeah,” Rory breathes out. That’s pretty much what she expected. 

“Do you know who the father is?” 

“Ah, the million-dollar question,” Rory chuckles softly. 

Lorelai sets her glass down. “And?”

Rory takes a deep breath, trying to keep a brave face. “Logan,” she says finally, and Lorelai’s eyes widen.

“That’s a doozy.”

“I’ll say.”

Lorelai hesitates before responding. “Have you told him yet?”

Rory shakes her head. “You’re the first person I’ve told.”

“Aw, kid, I’m flattered.”

“Yeah, well…” Rory sighs. “I only found out a week ago, anyway, so…”

“Hon, you’ve been carrying this secret around for a  _ week? _ ” Lorelai asks incredulously. “Rory…”

Rory nods. Suddenly, she feels like crying. “I didn’t want to take away from your wedding…” she chokes out. If she says anymore, she’ll start sobbing, which she does not want to do. Not today. 

Lorelai says nothing, but wraps an arm around Rory, bringing her closer. Rory rests her head on her mother’s shoulder, fighting to stay composed. 

“I’m scared, Mom,” Rory mumbles.

“I know, kid.” Lorelai sighs. “I know.”

They sit in silence for a while, Lorelai rubbing Rory’s arm soothingly. Eventually, Lorelai speaks, her bright tone just a little forced. “You sure it’s Logan? Because there are a  _ lot _ of eligible bachelors around here. I mean, maybe you had a little too much tequila, and some wine, and ended up in the arms of another man…”

Rory can’t help but chuckle. She sits up, wiping at her eyes with her sleeves. “I don’t think so. But it’s quite the concept, isn’t it?”

“Oh, totally. I can just picture it. It’s a quiet October night. There’s fog everywhere. You’re drunk and wandering through the empty, barren streets of Stars Hollow, almost passing out. But then, just when you think you’re done for, you spot him -- Kirk.”

“Hey, why do I get Kirk?” Rory interjects.

“Shh, I’m not done with the story yet.”

“Uh, you are if it’s  _ Kirk _ .”

Lorelai scoffs. “Kirk is a lovely man. I can’t  _ believe _ you would insult him like this.”

“Okay, then how about  _ you _ be the girl in the story.”

“Try again,” Lorelai objects, holding up her hand to show off her ring. “I’m spoken for.”

“So is Kirk,” Rory points out.

“Ah, shoot, you’re right,” Lorelai sighs. “Alright, then...Taylor.”

“That’s so much worse!” Rory exclaims.

“Well, you try to think of someone. There’s only so many men in Stars Hollow, kid.”

Rory shakes her head. “I refuse to be a part of this if it’s Taylor.”

“Has anyone told you how difficult you are?”

Rory exhales slowly. Her fear, for now, has faded -- she’s got Lorelai. That’s all she needs right now. “Thanks, mom.”

“Anytime, kid.” Lorelai returns the smile. They settle into comfortable silence for only a moment until she exclaims, “Jess!”

“What about Jess?” Rory laughs.

“The second single man we know. If we keep going, maybe we can expand the list to 3 whole potential fathers.”

They’re laughing, joking around, mother and daughter sitting in the gazebo, putting Rory at ease. She can feel the weight lifting off her shoulders, even if only for a moment. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Well, at least Luke looks guilty.

Jess isn’t thrilled to learn that his uncle and Lorelai eloped the previous night, sans Jess (for god's sake,  _ Michel  _ was there), but he decides he’ll carry on. He’s still a part of the reception, after all, and he just can’t leave Luke without a best man.

“Thanks?” Luke replies when Jess tells him all of this.

Jess claps him on the shoulder. “No problem, Eeyore,” he quips, prompting Luke to roll his eyes in exasperation.

Jess is crashing at Liz and T.J.’s for now, and truth be told, he’s ready to get out of the house. He loves his family, he does -- but the place is a mess, and it’s loud, and it’s crowded with eclectic furniture and boogie boards. Jess much prefers the solitude of his apartment in Philly.

So, he figures he’ll leave a day or so after the wedding. Luke and Lorelai leave for their honeymoon in a few days, and he decides he’ll be gone by then -- but this time, with a goodbye.

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Wedding headquarters has been moved to Miss Patty’s for the day of. The move was quick and messy, and nothing is in a designated spot. Despite the mess, Rory is still able to navigate -- it took her only a minute or two to memorize where everything is. The outfit she changed out of is hanging on a rack next to an old costume from one of Miss Patty’s recitals, by the table where Lorelai’s sewing kit sits next to Kirk’s camera (he insists on filming the wedding as part of his study on filming documentaries). Lorelai is making last minute adjustments to Doula’s dress, and Emily talks to her, Lorelai only replying in “hm”s and “sure”s.

Despite her proclamation to Lorelai this morning, Rory is elated. Her mother is getting married (albeit for the second time in 24 hours), surrounded by everyone she loves and everyone who loves her. This day could not be better, Rory’s sure of it. 

Jess stands off to the side at the mirror. He’s putting on his cufflinks and tie, and Rory pushes past the fluttering sensation she feels in her stomach upon seeing him in a white button-up. There’s just something about him now -- his air of confidence that replaced his deep-rooted insecurities, perhaps, or maybe it’s just the longer hair -- that makes her a little nervous and a lot happy. She’s thrilled to see that he’s made something of himself, and that he’s content with where he is. She used to wonder if that would ever be the case.

She has nothing better to do, so she walks over to him, and he smiles when he sees her in the mirror. “Hey, Gilmore.”

“Hey, yourself,” she breathes. “You handling that tie okay?”

“You know, you don’t have to monitor my attire. This isn’t the first formal event I’ve been to,” Jess intones, raising an eyebrow.

“When was the last one? A renaissance wedding in ‘04?”

“Alas, I did not wear a tie to that one,” he admits.

Rory laughs. “I think you’re a little out of practice.”

“Oh, yeah?” He turns to face her instead of watching her through the mirror, and Rory’s breath hitches at how close they suddenly are. “You think?”

“I do,” she agrees, and Jess smiles down at her, biting his lip. Emboldened, Rory crosses the remaining distance between them and reaches up and tightens his tie slightly. Her chest brushes against his as she fixes his collar, making Rory’s heart skip a beat. 

She takes a step back as if to admire her handiwork, but really, she needs to breathe. She’s not sure how she’d be able to handle being that close to him for much longer after all this time. “There we go,” she states. “Perfect.”

“Good work, Gilmore,” he replies, his voice pitched low. Rory breathes in and out, smiling. 

While the silence is heavy and full of uncertainty, it’s nothing new. Her relationship with Jess has always been a tricky thing. Rory’s determined to leave everything in the past, and she assumes he is, too. It’s difficult, though -- and while they definitely try to stay in touch, their communication has dwindled in the past nine years.

A month after her impromptu visit to Philadelphia, Rory finally worked up the courage to email him. For a while after that, their communication was frequent, but as with most long-distance communication, it faded over time. She sees him every few years or so, when he passes through Stars Hollow, and they’ll email now and then about books or work or something else impersonal. But it’s not like it used to be, and knowing that always causes her to feel something bittersweet. 

She’s never not happy to see him, though -- seeing him at the Stars Hollow Gazette this summer helped her immensely, and having him around for this wedding just feels right. Rory only ever really realizes it when they’re together, but she misses having him around her. She misses him a lot.

They’ve been staring at each other a little too much for comfort, she realizes. Jess must realize it, too -- he clears his throat, and Rory steps back, smoothing out the wrinkles in her dress. “So, uh…” She trails off.

“You look good,” he says, surprising both himself and her. There’s this look in his eyes that she can’t quite read — a swirl of emotion in his irises that’s only a little unsettling. 

Rory blinks a couple times, bringing herself back to reality. “Thank you,” she mumbles. “You do, too.”

Jess smiles again and nods slightly before turning to pick up his jacket and put it on. Rory wanders closer to her mother and grandmother, picking up the tail-end of their conversation. 

“...I just think it’s a little informal,” Emily is saying, evidently unaware of the fact that Lorelai is barely paying attention. “Getting married in the town square. It’s something out of a Nicholas Fire novel.”

“Do you mean Nicholas Sparks?” Rory offers, and Lorelai snorts.

Emily waves her hand in dismissal. “Doesn’t matter. All I’m saying is--”

“We have ten minutes until the ceremony starts,” Rory interjects. “Grandma, let’s go make sure our dresses are wrinkle-free.” 

Emily gives in, allowing Rory to steer her away, and Lorelai shoots Rory a grateful look. 

Throughout the next ten minutes, Rory’s heart pounds in her chest. The anticipation only grows with each passing moment.  _ Her mother’s wedding day. _ It sounds like a magical thing. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

The service is nothing less than perfect. The one the night before had been beautiful, too, but there’s just something about all of Lorelai’s friends and family smiling and weeping tears of joy that makes Rory’s heart glow. Even Emily has a handkerchief in hand as she watches. (The look on her face is similar to when Lorelai asked her to walk her down the aisle -- shiny eyes and a soft smile -- which is something you don’t often see on Emily Gilmore). 

Rory stands proudly at the altar as Luke and Lorelai exchange their vows, wiping her eyes at the particularly heartfelt moments. She catches Jess’ eye when Luke blows his nose into the microphone, both fighting off laughter. And when the groom kisses the bride and Stars Hollow cheers, Rory couldn’t be happier. She’s on cloud nine, and  _ nothing _ will bring her down tonight. 

The reception goes without a hitch. Rory gives her maid of honor speech, eliciting  _ aw _ ’s and hands to the heart from the crowd, and when she finishes, Lorelai catches her eye and mouths  _ thank you. _ Rory nods, grinning more than she thought possible. She might as well have forgotten about the baby -- there isn’t an ounce of negativity in her mind right now. 

Jess gives his best man speech next, and while Rory’s was sweet and soft, Jess’ brings many to tears. He recounts the time Luke pushed him in the lake and when they brought the ladle there to fight a swan, making everyone laugh. It’s when he sobers up and gives Luke a heartfelt  _ thank you  _ that everyone starts drying their eyes. “I wouldn’t be where I am -- or  _ who I am _ without him,” Jess says. “He taught me what it means to be a family.” He wraps up his speech with a witty joke, but everyone is still drying their eyes, even Luke.

Jess takes his seat next to Rory, fiddling with his sleeve. “That was a really nice speech,” Rory whispers.

Jess shrugs. “I call it like I see it,” he merely says, but his voice is low and gravelly, so Rory can tell he’s more emotional right now than he’s letting on. 

An hour or so later, the sun has set, but the party is still going. Kirk is struggling with his camera equipment, Babette and Maury are doing something that resembles dancing, and Sookie is dancing with her kids. Rory’s been talking to Lane for a while, but now she ambles over to her mother, who is talking to Liz and Jess. “Doula was such a good flower girl,” Liz is gushing when Rory approaches the group.

“Oh, definitely. Especially when she dumped the whole basket on the floor halfway through,” Jess replies. Lorelai snickers. 

“Be nice to your sister,” Liz reprimands him.

Liz wanders off to find T.J., mentioning something about tights, and is soon replaced by Emily, who begins to speak immediately.

“Lorelai, I was just talking to the most  _ wonderful _ man,” she declares.

Lorelai raises an eyebrow in disbelief. “You actually  _ like _ someone in this town?”

“Who was it, Grandma?” Rory asks before Emily can retort.

“Oh, it’s the fellow over there,” Emily gushes, gesturing towards Taylor, who is berating Jackson and Sookie’s kids for something or other while Jackson yells at him.

“ _ Taylor _ ?” Rory and Lorelai both say at once, shocked. 

Emily furrows her brow. “What do you have against him?”

Lorelai scoffs. “What  _ don’t _ we have against him?”

"Anyway, I brought up the idea of franchising his adorable little market--”

Lorelai groans. “The power will go right to his head.”

“What on earth are you talking about, Lorelai?”

Rory does not want this to go any further, so she redirects the conversation quickly. “Grandma, you’ve met Jess, right?” 

“Ah, yes,” Emily states flatly. “I see you don’t have a black eye this time.”

“I didn’t think it would match my suit,” Jess replies without missing a beat. Emily raises an eyebrow amusedly, but does not reply. “You’re up in Nantucket now, right?” Jess asks.

“Oh, yes and the drive up here was  _ hell.  _ There is so much construction. I mean, you’d think that they’d want to make the highway easy to drive on. That’s the whole point, is it not?”

“I’ve always thought so,” Jess replies. He catches’ Rory’s eye and winks. 

Emily nods curtly, but does not further the conversation. “I think I’ll get myself another drink,” she announces, evidently not keen on continuing the conversation.

“Rory and I can come with you and help you try to get Taylor’s number. We’ll be your wing-women,” Lorelai quips eagerly. Emily simply rolls her eyes and walks away, although there is a hint of a smile on her face.

-::--::--::--::--::--::--::--::--::--::--::--::--::-

It’s nearly one in the morning, but the festivities have not stopped yet. Rory hasn’t danced much, but she’s done some eating and talking, so she sits off to the side, content to just watch the party unfold.

Jackson and Sookie are dancing together; Lane and Zach are dancing with the twins; Kirk is chasing Petal; but the person that Rory is watching the most is Jess. 

Jess has ditched his suit jacket for the night, and the sleeves of his white button-up are rolled up slightly. He’s dancing with Doula, spinning her around and making her laugh. Rory can’t look away -- his smile is so bright, brighter than she’s seen it before, and it makes her so happy to see. 

As she watches him dance with his little sister, Rory sets her hand on her stomach, a lump in her throat. She’s been struggling to come to terms with the fact that she’s pregnant, the whole situation with Logan, but watching Jess with a little girl and a huge grin on his face is only complicating things for her. Rory doesn’t know when she’s going to tell Logan or what his response is going to be, and a part of Rory can’t help but think that if it was Jess…

No. She’s not going to do this to herself. She’s not going to think about what might have been or what could be if things were just a little different. No, she’s got a long road ahead of her, and she needs to face the facts. Nevermind the fact that Jess looks like the spitting image of a dad when he’s with his sister, or the strange feeling it evokes in her when she sees it. Logan is the father of her baby, not Jess. She shouldn’t be wishing otherwise -- especially after how she’s hurt Jess. It isn’t fair of her.

Luke and Lorelai are sitting together, both exhausted from dancing and thanking guests and general merriment. Lorelai’s eyes are fixed on Rory -- as happy as she is tonight, she can’t help but worry about her daughter, and what she’s going through. Lorelai knows what it’s like to be pregnant and alone, and it’s not a good feeling. But this is Rory she’s thinking about, right? Rory can do anything if she sets her mind to it. That has never been a concern.

“So, I had a brief conversation with Jess yesterday,” Luke mentions casually. Lorelai glances over at her husband (she’s unsure if she’ll ever get used to saying  _ husband _ ), eyebrows raised. 

“About what?” She intones. 

“Rory came out and showed him her book, so I asked him about it. It being...him and Rory.”

Lorelai blinks. “I’m waiting for the part that floors me, so keep talking.”

Luke recounts the conversation he had with Jess, ending by saying “So I guess it’s all in the past for good, huh? Jess and Rory?”

Lorelai snorts. “Sometimes I forget how naive you are. We need to work on your people skills during the honeymoon so you’re in tip-top shape when we get back.”

“Excuse me?”

Lorelai sighs in exasperation. “Look, even if Jess  _ says _ he’s over Rory, it doesn’t actually  _ mean _ he’s over her.” When Luke still looks puzzled, Lorelai groans. “Come  _ on _ , man. Do I need to spell it out for you, hubby?”

“Don’t call me  _ hubby _ .”

Lorelai dismisses his objection with a wave of her hand. “He’s not over her.”

“How are you so certain about this?”

“Years of practicing narcissism. I intend to be the next Robert Downey Jr.,” she replies. 

Luke looks unimpressed, so she carries on.

“Jess is the type of person to fall once and fall hard. Sure, maybe he takes some pit stops down the road, but he’ll always come back to her. If he still loved her years after he left, it’s very possible he still carries a torch for her.”

Luke blinks a couple of times. “Huh.”

“I told you, I’m really good at this. Freud is shaking in his boots. I’m the next Dr. Phil, but prettier and with a coffee addiction.”

“Freud and Dr. Phil aren’t even in the same ballpark.”

“Says you.”

“It just seems unlikely, that’s all. It’s been thirteen years.”

Lorelai doesn’t reply; she simply gestures towards Jess, who is still dancing with Doula. However, Jess’ gaze isn’t directed towards his sister -- instead, his eyes keep darting towards Rory, who doesn’t seem to notice. 

If she’s being completely honest, Lorelai feels for Jess, she really does. She understands better than most what it’s like to harbour feelings for someone she’s certain she’s lost -- and she just  _ knows _ that’s how Jess feels. Call it female intuition or ESP, but she’s sure of it. 

They watch as Doula runs over to her mother, laughing. Jess takes a step in Rory’s direction, hesitates, then crosses the distance and sits next to Rory. Rory jumps, but grins, and Jess smiles back, too. 

“Is this the moment?” Luke asks gruffly. 

“Not yet.” Lorelai shakes her head. “They’ve got a long way to go.”

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory doesn’t notice Jess until he’s sitting next to her. She jumps when he greets her, earning a chortle from him. “Did I scare you?” He asks, a teasing lilt to his voice.

“A little,” Rory admits. “I was just…”

“Lost in thought?” He suggests. 

Rory nods. “I’ve got a lot on my mind these days.”

Jess exhales slowly, drumming his fingers on the tabletop beside him. They sit in silence for a moment before he speaks again. “Alright. Well, I think I can distract you for the time being.”

Rory’s eyes widen. “How so?”

Jess merely smiles in response. He stands and extends his arm to her. “Dance with me,” he offers -- congenially, casually. The warm look in his eyes tempts her to take him up on it.

“What if I say no?” She’s teasing, flirting, and perhaps she’ll feel guilty for it later -- but she’s missed joking around with him, and he doesn’t seem to mind.

“Then I’ll be heartbroken forever,” he laughs. “It’s no big deal. Take it or leave it, you know?” Rory knows he means it, but there’s an edge to his voice -- one that suggests that his request isn’t as offhand and nonchalant as he’s acting.

“I’m not a good dancer.”

“So? This isn’t Dancing With the Stars.”

“I’ll step on your feet.”

“I’ve been hurt before.”

He raises his eyebrows expectantly, and she can’t help but smile. Rory tentatively takes his hand, fingers curling around his, and he gently pulls her up out of her chair. She follows him onto the dance floor, his hand warm in hers. 

Jess rests his hand on her waist, and Rory places hers on his shoulder. His other hand laces his fingers with hers, and they begin to move to the soothing voice of Etta James, slowly and stiff at first, but Rory allows herself to ease into his touch. She feels light and happy, her heart glowing when he smiles that crooked smile she’s always loved. 

Rory holds his gaze, and he holds hers, and there’s something shining in his eyes that makes her heart stutter. She stumbles, stepping on his feet, and the momentary spell is broken. Jess laughs, shaking his head. “How did you manage to step on both of my feet at the same time?”

“I warned you, I’m not physically gifted when it comes to dancing. I don’t know if I can manage much more.”

“You’ll have to swing it,” he replies simply.

Rory chuckles softly, and then they fall quiet again. The silence allows Rory’s mind to wander -- she’s able to focus on how close they are, his hand gentle on her waist, how smooth his hand is in hers, how their chests keep brushing against each other, how she can feel him breathing. Being so close to him only serves to throw her into the past -- how many April afternoons had they spent as close as this, pressed up against each other, falling for each other with every passing moment?    
There she goes again. She pushes these memories away to the back of her mind as she’s done so many times before, certain her feelings are gone. Because it’s so much easier this way -- friends and nothing more. She can ignore his hand on her waist or his chest against hers. She can ignore how broad his shoulders have become, how strong his arm around her is. And when he gets closer, and she loosely drapes her arms around his neck, she can ignore however it makes her heart jump. 

Because at last he’s here again, in Stars Hollow, right in front of her. Somewhere deep down he’s still her best friend, the one person she can count on to help her, to be there when she’s at her lowest without fear of judgement. At last, she can start to rebuild their friendship brick by brick. It’s hard work, sure, but it’s  _ good _ work -- and when she stares into his warm brown eyes, Rory is certain he wants it, too. 

  
  


**Notes for the Chapter:**

> they won't touch again until chapter 67 enjoy  
also check me out on tumblr (xliterati) and instagram (literatily)


	3. Let's Call the Whole Thing Off

**Summary for the Chapter:**

> After opening up to Lane, Rory seeks to catch up with Jess.

**Notes for the Chapter:**

> lowkey proud of this chapter tbh  
so the first week of school is done! i'm trying to prioritize my work, but i'm trying to finish the first draft of chapter 4 so i can post within the next week. hope you enjoy this chapter!

“And you’re you’ve got everything you need? And you have extra room in your suitcase for souvenirs?”

“Just call me Marie Kondo,” Lorelai replies, laying upside down on her bed as Rory paces back and forth with a checklist. 

“Sunscreen? Walking shoes? Passport?”

“You’re gonna wear the floor down to splinters.”

Rory stops her pacing, shooting her mother an unimpressed look. “Try going to the Bahamas without a passport and see what happens.”

“I have my passport.”

Rory points to the nightstand, where Lorelai’s passport sits under a gum wrapper and credit card. “Pack it.”

“I’ll remember it!”

“Just like you remembered your pants when we stayed in Maine three years ago?”

Lorelai rolls over so that she’s on her stomach. “I borrowed yours, it was fine.”

“You can’t borrow a _ passport. _”

“Fine, fine!” Lorelai gets off the bed, takes her passport and shoves it in her purse. “Happy?”

“Oh, just _ ecstatic _.” 

“So, how are you? You know, with everything?” Lorelai asks, plopping back down on the foot of the bed. She pats next to her, so Rory sits, too.

“Managing.” She lets out a deep sigh. “Just...managing.”

“Have you told Logan yet?”

Rory shakes her head. 

“Are you planning on it?”

Rory turns to face her mother. “How did Dad react when you told him you were pregnant?”

Lorelai exhales slowly. “Rory…”

“No, I want to know.” Rory’s voice is firm -- she _ needs _ to know. She needs to know what to prepare for. 

“Well…” Lorelai presses her lips together, hesitating before she answers. “I cornered him at school after last period. I told him with no prompting, and he just kinda stood there.”

“He didn’t say _ anything _?”

Lorelai laughs. “He was a regular Marcel Marceau.”

“And then?”

“He just said…’Oh.’”

Rory’s eyes widen. “Just…’oh?’”

Lorelai nods. “I had to give him a _ very _menacing look to get him to say anything more.”

“And?”

“He said, ‘So...this changes things.’”

Rory snorts. “That’s not much better.”

“No, it was not,” Lorelai agrees. “We both knew that having a baby at sixteen was going to make it very hard to go on with our wild hopes and dreams. But he was lucky -- he didn’t _ have _ to be a part of it.”

“But he wanted to at first,” Rory says, recalling only a few months ago when she had asked her father why he hadn’t been a part of her life.

“He _ offered _to. But his heart wasn’t in it.” Lorelai clicks her tongue. “I don’t think he would have been responsible even if he had helped raise you. He went off to do things, to try to become someone important. He didn’t want to be held back.”

“I’m scared Logan will react the same way,” Rory murmurs. When her mother doesn’t say anything -- no reassurance, no _ I’m sure he won’t _ \-- Rory laughs bitterly. “That’s what I thought.”

“I’m sorry, kid,” Lorelai sighs. “I don’t know Logan well, but he’s engaged. And across the ocean.”

“Guess you picked the right time to get a grip on reality, huh?”  
Lorelai smiles and shakes her head. “Had to happen sometime.”

“What am I going to do if he doesn’t want to be involved?”

“You’ll get through it,” Lorelai insists. “You’ve got a whole town of people who will support you and help you and love you. They’re the same people that helped me.”

Rory sniffles. “And what will I do if he _ does? _” She whispers. 

“Rory…”

She wipes her eyes with her sleeve, fighting back the tears that are threatening to spill. “I mean...I’m tearing apart his whole life. He’s _ engaged. _ He’s...he’s successful. I can’t take that away from him. But I can’t...I can’t do this by myself.”

“You won’t be by yourself, kid, you hear me?” Lorelai sets her hands on Rory’s shoulders, as if to shake sense into her. “You are _ not _ alone, with or without him.”

Rory nods and lets out a shaky breath. “Okay.”

“Now that that’s settled, how about we go through the checklist one more time,” Lorelai suggests, the corners of her mouth turning upwards. 

“We’re going to be _ very _ thorough,” Rory laughs shakily. 

“I know, kid. Now let’s get to work!”

-::--::--::--::--::--::--::--::--::--::--::--::--::-

“It’s _ fine _.”

“It’s gonna burn down, it’ll get robbed, it--”

“Look, you have _ got _ to calm down,” Jess reprimands Luke, shutting his book closed. “Caesar can handle the diner while you’re gone.”

Luke stops his pacing. “It’s not Caesar I’m worried about, Jess,” he says. “It’s this whole damn town! I am leaving my business undefended in the middle of a loony bin!” He throws his hands up in the air. “That’s it. I’m not going.”

“You’re going,” Jess insists. 

“Taylor will try to do something, I just know it. The second I leave, he’ll paint the diner red, or neon green, or magenta.”

“I hear magenta is all the rage nowadays,” Jess says offhandedly, going back to his book. He bites his lip in concentration as he raises the book and brings his pencil to the paper, scribbling down some notes in the margins as he goes.

“_ Jess. _”

Jess groans, setting his book down for the second time. “Look, if you’re this worried, I will stay a little longer and help out at the diner.”

“Don’t you have to be back in Philly?” Luke asks.

“I can stay a few days extra,” Jess reassures him. “Make sure Taylor knows not to mess with your business. That’ll take at _ least _ three to five business days.”

“Fine,” Luke relents. “But if _ one thing goes wrong _\--”

“Someone will pay.”

“Maybe you _ do _ understand me.”

Jess opens his mouth to speak, but there’s a loud _ bang _ upstairs followed by Rory’s laughter. Jess presses his lips together, opening his book again.

Luke stares at Jess, eyebrows raised. “You good?” He asks, only a little hint of mockery in his tone.

Jess does not look up. “Why wouldn’t I be?” 

“I don’t know. You were gonna say something, then Rory laughed, and you kinda...clammed up.”

“I’m fine.”

“Okay,” Luke concedes. “You know...you can talk to me about...you can talk to me, right?” He says, a little uncomfortable, but he means it.

“Yep.”

“And you’re _ sure _ you’re over her?”

Jess slams his book shut once again, exasperated. “What do you want from me? Do you want me to open up about the aching of my poor, broken heart? Eat ice cream out of the container and cry while watching Dirty Dancing? Because I don’t know if you heard me, but I am _ over _ this. It’s been ten years. How pathetic do you think I am?”

Luke blinks a couple times, processing all of Jess’ words. He knows Jess -- better than most -- and he’s seen this before, many times. Jess lashing out, hiding how he feels behind angry quips and snide remarks. And while Luke hasn’t conferred a self-help book in quite a while now, he _ knows _ Jess. He knows he’s hiding something, and he’s pretty certain about what it is.

“Sorry,” Jess mutters when Luke remains silent. 

“Well, when you poke the bear…” 

They both fall silent, and Luke can’t help but notice the tick in Jess’ jaw -- the way it’s set, clenched. 

“...Wait, you said it’s been _ ten _ years?”

“I did,” Jess grunts.

“But you haven’t been with her since 2003.”

“Right.”

“It’s 2016.”

“I can count, Luke,” Jess snaps. 

“So…”

“What?”

“You want to, I don’t know, explain?”

“Nope,” Jess says.

“But--”

“Drop it,” Jess warns him.

Luke sighs, and he drops it, sure -- but he can’t help but take note that when Rory laughs again upstairs, Jess’ jaw gets tighter.

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess is very much aware of the patheticness of his situation. He doesn’t need to be reminded of it by Luke.

He’s accepted it by now -- Rory is the only woman he’s ever loved, and she will continue to hold that title. And it’s sad, pitiable, he knows he has to _ move on _ \-- but then he hears her laugh or sees her smile and he’s so far gone he doesn’t even know where to begin. 

Rory has moved on. She’s dated, she’s loved, she’s _ lived _ \-- meanwhile Jess goes on a few dates a year, and nothing ever sticks. He plays nice, he asks questions, he’ll walk her home if she so desires -- there’s a one night stand here and there, but there’s never anything permanent. 

Not since her. Not since Rory. 

Luke prying only brings all this back to the surface. And Jess knows Luke means well, but the way he feels about Rory -- it’s something so deep and personal that he just _ can’t _ talk about it. He doesn’t want to start crying or something else. He just wants this to go away.

It’s foolish, he knows, foolish to stay -- but he’s always going to be indebted to Luke, and if he’s being honest -- really fucking honest -- he just wants to see her a little bit more.

So, he’ll stay in the apartment above the diner and he’ll work. Just for a little, just for a few days tops. He’ll see her again, talk a bit, and then go back to Philly. It’ll be fine, he tells himself.

It’s all going to work out just fine.

-::--::--::--::--::--::--::--::--::--::--::--::--::-

They leave for the honeymoon tomorrow -- the bags are (mostly) packed, thanks to Rory, and everything is all set, so they’re finally able to _ relax _. Lorelai and Luke sit on the porch together, taking in one last Stars Hollow night before they leave for two weeks.

“What were you and Rory laughing about this morning?” Luke asks suddenly, taking a sip from his beer.

“Oh, nothing, really,” Lorelai says. “We accidentally knocked the suitcase over, and were joking around.”

Luke nods.

“Why do you ask?”

“Oh, no reason. Just…” Luke clears his throat. “I was talking to Jess, and then he heard Rory laugh, and got all surly.”

“Wow, _ Luke Danes _ is calling someone surly. It must’ve been bad.”

“He was!” Luke insists. 

“Hey, pot? It’s kettle. You’re black.”

“_ Anyway _ ,” Luke says forcefully, “I asked him about it and he got _ really _ defensive.”

Lorelai shakes her head. “You poked the bear.”

“I know, I know…” Luke sighs. “But I wasn’t thinking. Well, I _ was _thinking, but about what you said -- how he’s not over her, right?”

“Right,” Lorelai answers. She’s curious to see where Luke is going with this.

“He mentioned how it’s been ten years, so he’s over her, but he hasn’t been with her since 2003. And when I mentioned that, he completely shut down.”

Lorelai lets out a long sigh. “Oh.”

“Oh?” Luke furrows his brow. “Do you know something that I don’t?”

“Aside from most things social?”

Luke ignores her comment. “Seriously, Lorelai, what am I missing?”

Lorelai hesitates before replying, and when she does, she speaks carefully, slowly -- so Luke _ knows _ this is important. 

“You know how Truncheon had that open house back in 2006?”

“The one I took April too, right?”

“Yeah,” Lorelai confirms. “That one.” She stares at the yard in front of her. “Rory went. Logan had just cheated on her, and she was upset…”

Luke’s eyes widen. “Something happened.”

Lorelai nods. “When it was over they were talking, and...they got their signals crossed, I don’t know...he kissed her. She kissed him back, but then...she was still with Logan, so she freaked.”

Luke exhales slowly. “That’s…”

“And I don’t remember the specifics, or if Rory told me everything they said...but she told him how she was still with Logan, how he cheated on her, but how she still loves him despite it...and I guess he was understanding, or at least he didn’t fight her on it...but she left.”

“Damn.”

“Yeah.”

Luke shakes his head. “That explains why he was...acting the way he was.”

Lorelai sighs. This is one of those moments, one of those moments where she has this urge to _ fix _ \-- she wants all of the people she loves to be happy, and that includes Jess. Maybe it took a while to get there, and maybe it’s a little too late, but Lorelai can understand. What it’s like to _ almost _ be loved, to almost be _ in _ love _ , _ to be so close that it hurts. And if she’s right, if her suspicions are correct, Jess would most definitely agree. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory’s still a little scattered these days.

She’s consolidating all her belongings and working towards renting an apartment in Queens, and while it’s slow going, it’s going good, and she thinks she’s finally in a secure enough place to tell someone else.

She’s laying on the floor of Lane’s bedroom while Lane sits in a bean bag, periodically taking a chip out of the bag and eating it. “Woah,” Lane says for about the millionth time. 

“Yeah,” Rory says, for the millionth and one.

“Woah.”

“Lane, if you say ‘woah’ one more time, I’m going to lose it.”

“It’s just--”

“Woah,” they say at the same time.

Rory lets out a long, deep sigh, staring at the ceiling. “I’m still coming to terms with it myself.”

“Have you thought about how you’re gonna tell him?”

“A lot more than I should,” Rory admits. “I’ve got a thousand different scenarios, and I’ve replayed them all a hundred times.”

Lane smiles. “Always prepared.”

“That’s me.” Rory closes her eyes. “I’m terrified, Lane. I know I’ve said that so many times, but…” She lets out a shaky breath. “I just keep coming back to it.”

“I was scared, too,” Lane says, mouth full of chips. “I thought Zach was going to freak, or bail...I thought I would be horrible. You remember how nutty I got.”

“But you have _ Zach _ ,” Rory moans. “You were _ married _. Logan is engaged and in another continent. He has every right to bail.”

Lane sighs. “Maybe. But if he does bail...maybe you dodge a bullet either way.”

“Lane…” Rory swallows, trying to work up the nerve to ask the question she’d been afraid to ask. “When you first found out you were pregnant, did you ever...did you ever wish the father wasn’t Zach? That it was...someone else?”

Lane pauses, thinking out her answer before she speaks. “A little,” she admits. “Only at the very beginning. I kept thinking...what if it was Dave? He was so reliable, and Zach hadn’t always been, so I just...wondered.” When Rory stays silent, Lane leans forward, concerned. “Why do you ask?” She says softly, even if the answer is obvious.

Rory takes a deep breath before answering. “At the wedding, I was sitting by myself, and I was just thinking…what if it was someone else?” She can’t bring herself to say his name.

“Who?” Lane asks, curious. When Rory doesn’t answer, Lane gasps. “No. _ Jess _?” 

Rory has a weird urge to smile. Lane knows her so well. “Yeah,” she breathes out. “He was dancing with Doula, and I just…”

Lane exhales slowly. “_ Jess _,” she repeats. “Do you still have feelings for him?”

“No,” Rory says firmly. “No.”

“Then why…”

“Seeing him dancing with Doula…” Rory winces. “He looked so...fatherly, I don’t know. And the fact that he has his life together...he’s not having affairs or making lame excuses for himself...I think I was just projecting,” she concludes. “I want to be reliable. I want to be responsible. He is, and I’m...I’m not.” 

Lane nods. “Okay. I can see where you’re coming from.”

“I guess I’ve just gotten used to him bailing me out, you know? Setting me straight? He got me to go back to Yale, he gave me the idea for my book…” She groans. “It’s stupid.”

“It’s not stupid,” Lane insists. “It’s not. You’re scared, and you want someone reliable.”

“It’s kinda funny,” Rory says. “That we used to sit like this and talk about how _ unreliable _ Jess was.”

Lane chuckles. “Times change.” She shrugs. 

“A little too much,” Rory sighs. 

“Maybe,” Lane says, “but it is what it is, you know?”

“Yeah,” Rory breathes out. _ It is what it is _ conjures up a memory, and she fights to push it away. It’s unfair of her to be so dependent on Jess. If she’s over him -- which she is -- all she’s doing is using him. And that’s just one more thing she can add to the list of things she regrets.

Lane munches on another chip. “Maybe you should meet up with him,” she suggests. “Talk. Catch up. Learn the gritty details on his life. Get this ‘Jess is perfect’ idea out of your head.”

“He’s probably in Philly already,” Rory laments. 

Lane furrows her brow. “I saw him in the diner this morning.”

Rory props herself up on her elbows. “What?”

“Oh, yeah, I was walking by with the boys and saw him through the window. He was behind the counter and everything.”  
Rory bites her lip. “We’re not really that close, though. We’re not... _ friend _ friends.”

“Don’t you want to be?”

“it would be nice,” Rory admits. 

“So...try!”

Rory shakes her head. “If he’s working, I don’t want to bother him.”

“Hey, stop making excuses,” Lane reprimands her. “Think to yourself: do you want to be his friend? If the answer is yes, then go for it. If the answer is no, then don’t.”

“I’m sorry for this,” Rory says softly. “I’m just…”

“You’re going through a lot,” Lane shrugs. “There’s nothing to apologize for.”

“I have to tell Logan,” Rory says. “I have to.”

“One thing at a time. Pace yourself.”

Rory smiles at her friend. “I’d be dead in a ditch if it weren’t for you.”

“Right back at you.”

Rory lays back down, her mind racing. She knows that she’s doomed to repeat her old mistakes if she keeps going like this -- she has to make up her mind. Not knowing what she wants has only ever lead to disaster. Being with Dean and having feelings for Jess, being with Jess and being hung up on Dean...she only ever hurts the people she loves when she’s conflicted. 

Once upon a time, she didn’t want to love Jess. And once upon a time, she didn’t want to love Dean. And right now, she finds herself wishing she didn’t love Logan. And she hates herself for it.

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess wipes down the counter, only half listening to Kirk. He’s talking about his new hair care product or something, Jess isn’t really sure what it is -- but Jess tells himself he’ll be gone in a few days, so he’ll just deal with it. 

The bell jingles as the door opens, and Jess freezes when he hears her voice. 

“Come on, Kirk, leave him alone,” Rory insists, and Jess can’t help but smile softly. 

She shoos Kirk away before sitting down at the counter. “Good morning,” she says brightly.  
He nods. “Mornin’,” he says before looking back down and continuing to wipe the counter. 

“So, you’re working in the diner?” She asks.

“Just for a few days,” he replies. “You know, Luke has some serious issues regarding leaving the diner alone. He was half convinced Taylor would start a coup.”

Rory laughs, and Jess hates how his heart twinges at the sound. “Sounds like him.”

“So, what can I get for you?” 

“Coffee, please? Decaf,” she adds hurriedly, and Jess raises an eyebrow.

“Since when do you drink decaf?” 

Rory shifts uncomfortably. “I, uh…”

“Hey, I’ll get you the decaf,” he assures her. “For here or to go?”

“For here,” she decides, her face a little flushed. Jess nods, and he turns and starts to make it, biting back his questions. She’s acting a little odd, but he decides to chalk it up to them just not having spoken a lot in a while. There’s no reason to jump to conclusions. 

He turns around and hands her the mug, and she smiles gratefully when she takes it. Their fingers brush, and it’s hardly noticeable, but Jess’ heart still flips. 

Rory takes a sip and sets the mug down. “How long exactly are you staying?” She asks carefully. 

“Trying to get rid of me, Gilmore?”

She smiles. “I might be.”

“I’ll probably leave in a day or two.”

Rory takes another sip. “Where are you staying?”

“Apartment upstairs,” Jess says, gesturing upwards. “Luke’s kept it, and it’s convenient, so…”

She nods. “God, I haven’t been up there in ages.”

“It’s a trip down memory lane, that’s for sure.”

She pauses again, stopping to take another sip of her coffee. “We should catch up,” she says suddenly, startling even herself.

Jess takes a moment before replying. “I’d be up for that,” he says simply. Rory grins, and Jess’ heart is suddenly doing acrobatics in his chest. He bites his lip, trying to hold himself back from grinning like an idiot. She has that effect on him -- she makes him want to be vulnerable. She always has.

“When do you get off?” 

“I can come and go whenever I please,” he smirks. “Perks of being in charge.”

“Good.” She looks away and then looks back, a little jittery. “Want to go now? To Weston’s, maybe?”

“I’ll get my jacket.”

“Good,” she repeats, and her smile is enough to make him think that maybe, just maybe, he was right in staying. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

“How can you say that?” Jess exclaims. “That wasn’t the point and you _ know _ it.”

“It was!” Rory insists. “_ A Heartbreaking Work of Staggering Genius _ is a coming-of-age story. It’s practically spelled out for you in the first chapter.”

“You’re delusional,” Jess laughs. 

“You’re stubborn.”

“I’m _ right _.”

She laughs, shaking her head. “I guess we’ll have to agree to disagree.”

“For now.” Jess glances at her before looking down and taking a bite of his pie slice. Rory catches this twinkle in his eye, and it creates an odd feeling in her stomach. (Or maybe it’s just the morning sickness.)

“So, we haven’t gotten to the main purpose of this outing,” she announces.

“Which is…”

“To catch up,” Rory declares. Jess nods slowly and takes another bite. “So, what’s new with you?” 

“Nothing, really,” Jess replies nonchalantly. “The press is going good. We’re considering expanding, but we’re not quite sure if we have the money. It’s all up in the air.”

“That’s good!” Rory exclaims. Jess merely shrugs. “It is,” she insists. “It’s about time you guys expanded. Truncheon has so much potential.”

“You’ve always believed in us,” Jess murmurs. 

“I have.”

Jess smiles that crooked smile, and Rory’s heart twinges. “I’ll tell the guys you think we should expand.”

“Good.”

“How’s your book?” Jess inquires, and Rory’s smile grows wider.

“Oh, it’s so good, Jess, you have no idea,” she breathes. “I’m already, like, six chapters in.”

“That’s great, Rory,” he says.

Rory’s smile gets even wider. “It is, isn’t it?” When he smiles back, the odd feeling in her stomach grows. She has a question to ask him, and she’s a little scared to ask -- but it’s important, and who knows, maybe he’ll understand.

“How far into your life is your book going to go?” Jess asks casually. “I’m assuming you’re not going to go much further than college, right?”

“I’m thinking I’ll stop either at the end of high school or college,” Rory says, then adds cautiously, “which reminds me, I have a question for you.”

Jess raises an eyebrow. “Shoot.”

She swallows, trying to battle the anxiety she’s feeling. “You were -- are -- an important part in my life,” she begins. “Especially when I was in high school.”

“And?” He prompts her, but he sounds like he already knows what she’s going to say.

“I was wondering if I could put you in the book,” she says nervously. “I’d change the name, definitely, but I need your permission. I wouldn’t feel good about it if I didn’t ask.”

Jess is silent for a moment before he speaks. “Is this the reason you asked me here?” He teases, making sure she knows he isn’t serious.

“It’s strictly business,” she chuckles.

He’s quiet again, and Rory can feel the nerves coming back. He’s going to get mad, he’s going to say no, he’s going to --

“It’s your life,” he says finally. “This is _ your _ story, Rory. If something -- someone -- if...if _ I _ had an impact on you, and it’s important to you, then write it.” He looks her in the eyes, and it’s like the rug has been pulled out from under her. This isn’t the reaction she was expecting, not at all. “The book only means something if it’s _ honest _. Don’t dance around the truth because you don’t want to offend. Look at all the people in your life, and reflect.”

“Jess…” She’s unable to find the words right now, but she’s grateful. She’s so, so grateful.

“Put me in your book,” he continues. “It doesn’t matter what I feel about it. You can use my name or change it, whatever feels right. This book needs to feel right to you. It needs to be real. Raw. Vulnerable.” He holds her gaze. “Write what feels right.”

“Thank you,” is all she’s able to say, her voice hoarse. 

He looks over at the clock. “I have to get back to the diner,” he informs her. He stands up and puts his coat back on. Right before he walks out, he looks over his shoulder at her. “I’m looking forward to reading it.”

The door closes behind him, and Rory sits there, going over what Jess said. She’d been so worried he would get mad or defensive or clam up, but he hadn’t. He hadn’t reacted like Dean, either -- concerned about what she would write, needing reassurance. He’d reacted like _ Jess _, she realizes. Jess always wanted what was best for her, even if he was bad at showing it. And she knows she needs to stop depending on him for these profound revelations -- she needs to figure things out on her own, to find her own way. But at least he’s a constant -- reliable. And knowing that she can trust him is the first step towards rebuilding their friendship. And that, she figured out herself. 

  


**Notes for the Chapter:**

> hmu on tumblr (xliterati) or instagram (literatily)


	4. Here You Come Again

**Summary for the Chapter:**

> Jess should probably listen to Chris and Matthew, but he's not quite ready to go. Rory works up the courage to tell someone else.

**Notes for the Chapter:**

> sorry this is lowkey a filler chapter but i promise they'll pick up from here

Jess wonders if he’s ever going to leave.

He misses Truncheon, and Chris and Matthew, and then he sees Rory, and everything flies out the window. He’s well aware that he’s digging his own grave, setting himself up for disappointment, but it’s so tempting to do so. 

It’s only been a couple days extra, but he keeps finding excuses to stay -- keeping an eye on the diner, messing with Taylor, or even just getting a kick out of this walk down memory lane is enough to convince him to stay. 

Stars Hollow is the same as when he left it, but it’s so different, too. He knows he’s changed, too -- he’s changed a _ lot _, a change that might be jarring, transforming from an immature, troubled teenager to a mature and put-together adult. He’s come a long way -- long enough that he’s proud of himself, that he’s glad he turned it all around. And while at first he didn’t care what the town thought of him, falling in love with Rory had changed all of that. And, yeah, he’s not with her now, but he can’t help but feel good when Patty waves to him when he walks by the studio or when Babette buys him a cup of coffee at Weston’s. The place that was once a prison has become an escape, a home away from home -- a place he’ll always be attached to. 

And then, there’s Rory. Rory is the heart and soul of Stars Hollow, the girl everyone loves, the girl you just can’t walk away from, no matter how hard you try. He’s well aware it’s her that’s keeping him here, but he just doesn’t want to say goodbye to her. Goodbyes hurt, and he’s just not ready. Not yet. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

When he decides to stay until Luke gets back, Jess decides to call Chris and Matthew to update them. “I’m staying here for a few more days,” he informs them, and they both groan.

“You keep putting us off,” Matthew complains. “Does Truncheon even _ matter _ to you anymore?”

“I told you, my uncle needs help with his diner,” Jess explains for what feels like the hundredth time. “He’s on his honeymoon and he’s paranoid about leaving it unprotected.”

“That’s what you said two days ago,” Chris says from a distance. 

“Tell Chris to shut up.”

“Chris, Jess says to shut up.”

“Besides,” Jess continues, “it’s been a while since I’ve seen all these people, you know? It’s been a while,” he repeats. “Oh, I almost forgot to mention -- Rory votes yes on expanding. And, you know, I think she may have a point.”

There’s silence on the other end, and Jess knows Chris and Matthew are exchanging wary looks. “Jess,” Matthew says slowly, “You’re talking to Rory?”

“...Yes,” Jess admits, and when Matthew groans on the other end, he defends himself, saying, “But, it’s fine. We’re friends, you know?”

“You’ve been in love with this girl for, like, fifteen years,” Matthew replies. “Do you really think it’s a good idea to be staying in the same town as her? I mean, does your uncle _ really _ need your help?” When Jess stays silent, Matthew exclaims, “ _ Seriously _? Are you staying there for her?”

Jess runs a hand through his hair. “I don’t know. I’m not going to lie, it’s been really nice seeing her.”

“How much have you been seeing her?”

“We talked for a little while today, and it was good. It was really good.”

“This isn’t healthy,” Matthew reprimands. “Do you need me to remind you of what she did to you ten years ago?”

“No, you don’t.”

“You were _ heartbroken _, man,” Matthew says, but softly this time. “You remember?” Jess bites his lip -- of course he remembers. He remembers how drunk he got that night, trying to push away all of his feelings, struggling to forget. He remembers the way his stomach plummeted when she told him she was still with Logan, how his heart broke when he watched her leave, how long it took him to move past it. 

“I know. I just…” he runs his hand down his chin. “She’s still a part of my life. Always will be. And I’m good with being her friend. That’s a lot more than I deserve.”

“This is just sad, man.”

“I’m well aware.”

“Be careful, Jess,” Matthew warns him.

“Always am.”

Jess gives him a “see you later” and hangs up, but Matthew’s words still stick with him. He’s being careful, he knows he is. He never sees her outside the diner, and he always leaves the counter between them. Keeping his distance is hard, sure, but it’s necessarily. He’s being careful. But is it enough? When he leaves, and it’s inevitable, he’ll be saying goodbye to her again. It’s always the worst part, goodbyes. He’s never liked them much. 

Everytime he says goodbye, it breaks him just a little bit more. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

_ The door clicks shut. _

_ Jess stands there, and he’s not sure _ why _ he’s still standing there -- he should be doing something else, getting his mind off this heartbreak that’s threatening to swallow him whole. _

_ But he can’t move on, and that’s the thing _ \-- _ he’s been trying to move on for three years. And he didn’t. And now, because of that, his heart is in his throat, and tears are fighting to fall. He feels weak. He feels weak and stupid and lost. _

_ He had been so happy to see her. Nervous, too, but happy. What a rare occurrence. She showed up, and he hadn’t thought she would -- it filled him with hope. To have all that happiness and hope knocked out of him with a single blow...well, it doesn’t feel good. _

_ This time it wasn’t on him, but it’s a small relief at best. Because, when you get down to it, their perpetual situation _ is _ his fault. He left, he messed it up, and now, three years later, he’s lost her again. (Not that he ever really had her to begin with.) _

_ They’re never going to be anything again. This was the final nail in the coffin. He did everything right this time, and he wasn’t enough. She’s in love with Logan (that asshole), who _ cheated _ on her, and Jess hates him for it. _

_ He hates anyone who’s hurt Rory. _

_ So, he hates himself, but that’s not new. _

_ Jess knows all of this. He’s utterly and painfully aware of the fact that they’re off the table, so much that the majority of him wants to break down crying. But he’s fighting it. His throat hurts from holding it back, but he’s not going to give in. _

_ They’re not going to be anything ever again. _

_ But, life moves on. _

_ So, he wipes his eyes and drives to the bar, the one they’re not calling Cedar Bar Redux, to drink. To make everything stop for just a moment. _

_ “Jesus, man, are you okay?” Chris asks, puzzled, as Jess works on his third beer. He hasn’t spoken at all -- just to order -- he’s just drinking. _

_ “I’m fine,” he mutters. _

_ “The empty bottles beg to differ,” Matthew points out. _

_ Jess bites his lip. He’s drunk, yes, but because he wants to forget completely -- he wants this to go away. But he knows also that Chris and Michael will keep asking, and he’ll only get drunker, so, really, he doesn’t have a choice. And he trusts them, he really does -- he’s confided in them before -- so, he’ll talk. Briefly, and then move on forever. _

_ He sets down the bottle and clears his throat. “Rory came by today.” _

_ “Rory?” Chris asks, puzzled. _

_ “My ex.” _

_ Matthew shakes his head. “Oof.” _

_ “We’re friends now, friendly -- we were, anyway. When I was in Connecticut distributing my book, I stopped by and talked to her. So I invited her here, thinking she wouldn’t come. She’s got this boyfriend--“ _

_ “Man…” _

_ “I met him when I was in Hartford, and he was an _ asshole _ . But she came here, alone, so I thought, maybe…” _

_ He trails off. “So that’s why you said you’d catch up with us,” Matthew realizes. “You thought…” _

_ Jess nods. “I thought that maybe...maybe something would happen.” _

_ “You still got a thing for her?” Chris inquires, eyebrows raised. _

_ “A thing,” Jess laughs bitterly. “I wish that’s all it was.” _

_ Matthew’s eyes widen. “How long has it been since you dated?” _

_ “Three years.” _

_ “Damn.” Chris whistles. _

_ Jess sighs. “I thought maybe something would happen.” He repeats. _

_ “But it didn’t, did it?” Chris guesses. _

_ Jess scoffs. “That’s the thing, isn’t it? Wouldn’t it have been better if it didn’t?” _

_ “Oh, man…” _

_ “I kissed her.” _

_ Siilence. _

_ “She kissed back.” _

_ Matthew lets out a deep sigh. “Where does this go bad?” _

_ “She kissed back, but only for a moment, and then she freaked. She was saying how she was being unfair and she couldn’t cheat on him like he did to her…” _

_ “So she kissed you and then freaked,” Matthew sums it up. _

_ “She kissed me back,” Jess says bitterly. “She let me think...she let me get my hopes up. But then she says she’s still in love with the bastard, and she’s still with _ him _ …” He spits out the word _ him _ with such venom, so much hurt, that Matthew winces. _

_ Chris shakes his head. “That’s fucked up of her.” _

_ “Stupid, really,” Matthew agreed. _

_ “She’s dead to us,” Chris adds. _

_ “I love her,” Jess mutters. “So who’s stupid now? I’m the one who fucked it up in the first place. And now…” He takes a sip from his beer. _

_ Chris and Matthew make eye contact, not saying anything, no doubt concerned about him. _

_ Jess sighs. “I just want to drink, okay?” _

_ “Okay, man,” Matthew says, eyes wide. _

_ They fall back into silence. Jess orders another drink, and one more for good measure. He wants the world to be fuzzy and quiet, and it is -- for one quiet moment, he’s forgotten. He’s forgotten his pain and heartache and everything in between. _

_ It won’t be enough in the morning. This will torture him for a while, he’ll learn to live with it -- it turns into a dull ache, and it stays that way. He learns to move past it, but not to move on. That’s so much harder to do. _

_ It’s a painful way to go, he thinks. Loving and then losing and then loving again, but it’s only halfway there. _

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory misses her mom. It’s only been five days, but it’s five days too many -- she needs her best friend. She needs to talk, needs a distraction. But she knows she has to accept her reality. So, she decides to tell someone else.

She tells Paris. Or, Paris guesses within five minutes of the phone call, and Rory is stunned, and the call is over in the next ten. But, that’s one more person who knows. One more person closer to telling Logan.

So, Rory goes to the diner afterwards, feeling a little relieved. She needs some coffee and maybe a burger. She walks in, and when she sees Jess behind the counter, she freezes. She thought Jess would be back in Philly by now -- but if she’s being honest, she’s happy. She hadn’t fully realized it until now, but she wanted to see him again. 

“You’re still here,” Rory observes, walking up to the counter.

“I’m still here.”

“I thought you were going to leave after a couple days,” she says, sitting down. 

Jess shakes his head. “I know, but I think me being here is unnerving Taylor. He half expects me to start drawing chalk body outlines and steal some gnomes.”

Rory cocks her head to one side. “Are those worries warranted?” 

“Fifteen years ago, maybe,” Jess shrugs. “But it’s fun. He keeps watching me through the window. I like to pretend to almost drop things just to freak him out.”

Rory laughs. She likes this -- this being talking to him again, joking, just _ being _ there with him. It’s been a long time since they’ve been like this. 

“What brings you here?” Jess asks casually. 

“Oh, nothing, really. Just got off the phone with Paris, so--“

“Say no more.” Jess turns and when he faces her again, he has a mug and the coffee pot. He pours her some, and then says “a talk with Paris warrants at least three of these.”

“Thanks, Jess,” she says. She eyes the coffee warily, like it might attack her. “Is it--“

“It’s decaf, yeah, you weirdo,” he reassures her. Rory laughs softly. “Jeez, you were looking at that cup like you had to decide if it was poisoned or not. Have you been watching the Princess Bride lately?”

“Not recently, no.”

Jess laughs, and Rory’s stomach is doing somersaults -- not necessarily because of him, but what’s on her mind. This question she wants to ask. This question that has been on her mind ever since the wedding. “Jess,” she says slowly, “have you ever...have you ever thought about having kids?” _ Please don’t let him guess. Please don’t let him figure out my secret. _

“Kids?”

“Yeah,” she confirms. “Kids.”

Jess’ brow furrows, and for a terrifying split-second, Rory is _ positive _ he’s figured it out. But then, he says, slowly, “I’m not sure,” and she can breathe. “I guess...If I found the right person…” He frowns. “It would be a discussion.”

“A short one?”

“Not necessarily, no,” he says, a serious answer to a teasing question. “It’s not a priority, but, if it happens…”

Rory nods.

“What makes you ask?”

“I don’t know,” she says nervously. “Just curious, I guess.”

He nods, not saying anything, which makes Rory’s heart start beating a million miles a minute. _ Does he know? Why did I ask? _

But then he smiles and shakes his head, turns around, taking plates from Caesar and bringing them to their tables. And as she watches him, Rory finds herself wondering why she was so terrified he’d figure it out. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory’s been acting weird. Jess has been noticing it all week, and he hasn’t said anything because he knows it’s absolutely none of his business, but if he’s not curious, he’s concerned. 

Jess won’t let himself try to figure it out -- if she wants him to know, she’ll tell him. So, instead, he focuses on her question. _ Have you ever thought about having kids? _ And the truth is, yes, but not in the way you’d expect. 

Jess hasn’t thought about kids because there’s no one to _ have _ kids with. He was telling the truth when he answered Rory -- it’s not something he’s seeking out, but if he ever finds someone, he’s open to it. And, if he’s being honest, the idea of raising a kid and trying to be everything his parents weren’t is appealing. But, then again, his heart will always belong to Rory, so where does that leave him?

Besides a couple dreams from his teenage years that seriously freaked him out, he’s never entertained the fantasy of starting a family with Rory. Or, really, he hasn’t let himself. 

Jess figures he’ll be single for the rest of his life, but it’s something he’s come to terms with. So, it’s okay. _ He’s _ okay. It’s really, really, okay.

-::--::--::--::--::--::--::--::--::--::--::--::--::-

_ If Jess has another one of these dreams, he’s going to have to see a shrink. _ _  
_ _ He’s been dating Rory for a couple months now, and it still catches him off guard. He’ll be sitting on the couch with his arm around her and suddenly think -- wow. I’m dating Rory. It’s something he never thought would actually happen, and while he’s still terrified of messing this up, he’s appreciating every moment they have together. Because, well, he loves her. He knows this, and he’s known it for a while now. So it was really only a matter of time before he started having these dreams. _

_ It always starts the same way. He wakes up in the apartment above the diner in a big bed, puts on a shirt and sweatpants, and goes down the stairs. When he gets downstairs, he’s not in the diner anymore. Instead, he’s in the Gilmores’ kitchen, where Rory sits at the table reading a newspaper. She has reading glasses on. He always goes over to her and kisses her before starting to make some breakfast. That’s when it gets really weird. _

_ He turns around to say something to Rory, but she’s not sitting at the table anymore. Instead, she’s walking out of her old bedroom with her glasses perched on top of her head -- oh, and she’s holding a baby. _

_ Different things happen after that. Sometimes more kids run in, or sometimes it’s just the one -- but it’s the kid part that freaks Jess out. _

_ He’s dreaming about having kids. With Rory. Now, he’s not big on dream-interpretation, but this has to mean _ something _ . He’s eighteen, for crying out loud. This isn’t the type of Rory-related dream he should be having. _

_ He would never bring it up to her, not in a million years -- it’s too much, too forward, and would probably send her running for the hills. _

_ He knows it in his heart that their romance is fragile. The slightest slip-up could cost him everything -- he could lose her if he does the slightest thing wrong. He’s not Dean, he’s never going to compare to Dean, and that’s always on everyone’s mind. _

_ This relationship won’t last. She’ll leave him for Dean eventually. So, these dreams don’t matter. And even though he loves her -- which he really, really does -- he pushes these dreams to the back of his mind. Something he’s so used to doing. _

-::--::--::--::--::--::--::--::--::--::--::--::--::-

It’s been two weeks since she’s found out, but Rory still hasn’t told Logan about the baby.

She sits at her desk, staring at her cell phone, willing herself to pick it up. This is a common occurance now -- she finds herself here a lot nowadays. Her laptop is open, but she’s set it aside for now. Instead, she sits there, trying to force herself to call.

She and Logan haven’t spoken since their last time together that October night. They’ve done everything but cut ties -- she hasn’t deleted his number or even pictures of him in her camera roll. It’s too hard. She already has a Logan box in the front hall closet. She’s trying to treat it like any other breakup, but it’s not -- she kept finding herself going back to him. He was familiar, comforting, someone who never questioned her or judged her when she was at her lowest. But if he’s so good, why is she so scared to tell him that she’s pregnant? 

Her phone rings, startling her out of her stupor. Heart pounding, she scrambles to pick up -- is it Logan? Did she conjure him?

She checks the caller ID -- it’s not Logan.

“I was going through some boxes,” Lane says immediately after Rory picks up, “and I found some stuff from when I was pregnant with the boys. Some cute little parenting books, pregnancy books, and some other stuff. I thought you might be interested in some of it.”

Rory smiles to herself. “Thank you,” she replies. “I might, yeah.”

“You can come over later and look through it?” Lane suggests. “And if you have any questions, you can ask -- I know you have your mom, but for when she’s not available…”

“No, I’d really appreciate that. Thank you so much.”

“Anytime, Rory.”

Rory exhales slowly. “I guess I’m really doing this, huh?”

“I guess so.” Pause. “Have you...you know, told Logan yet?”

“No,” Rory admits ashamedly. “I just...can’t get myself to.”

“Well, keep telling other people. Work yourself up to it.”

Rory leans back in her chair. “Like who?”

“I’m not sure,” Lane says. “Your grandmother, maybe?”

“Oh, god, no.”

Lane snickers. “Okay, okay. Hm...what about Jess?”

“Jess?”

“I mean, you’re catching up, no?”

“He _ hates _ Logan,” Rory sighs, biting at her nails. “Plus, I just don’t think we’re there yet.”

“He’ll find out eventually. Everyone will. Might as well tell someone.”

“I told Paris,” Rory offers.

Lane laughs, and they talk, moving on to other topics -- the band, Rory’s book (Lane says Rory can _ absolutely _ put her in the book), or the boys. When Rory says goodbye and hangs up, she brings her knees up to her chest and sighs. Lane is right, and she _ knows _ that Lane is right. She has to rip off the bandaid. She has to come to terms with this -- fully, and fast.

She pulls her laptop closer to her. She’s been working on the book a lot this week -- it’s a distraction, and she’ll admit it, but at least it’s productive.

It feels good. To be proud of something. To _ create _ something. 

She picks up her phone and types out a text to Jess. _ Thank you, _ she writes. _ For giving me this idea. I have a draft to share over coffee if you want. _

She presses send, and he replies within the next minute. _ Oh, definitely, _ he replies. _ Meet me in the diner tomorrow at 1:30? _

_ See you there, _ she texts back. Then -- _ I can’t wait for you to see it. _

_ Right back at you. _

-::--::--::--::--::--::--::--::--::--::--::--::--::-

_ “Jess, please,” she begs for the millionth time. _

_ “It’s not going to do you any good,” he replies, but he takes her essay from her all the same. _

_ “You don’t know that.” _

_ “Fine,” Jess says, already reading. “You’re annoying, you know that?” _

_ Rory laughs. “I think I’ve been told that before.” _

_ She falls silent as she watches him read her work. Twirling his pencil between his fingers, scribbling down notes every now and then, brow furrowed as he concentrates. She likes the way he looks when he reads, something she can admit to now that they’re together. She likes the way he cocks his head to the side, how he bites his lip in concentration -- and now, how he looks up grinning when he’s done reading her work. _

_ “A plus,” he announces, sliding it back to her across the table. _

_ She looks down at the paper, her heart leaping when she sees his handwriting on the page. She doesn’t even need him to go over her work -- she just likes hearing his opinion. She likes reading his feedback and comments. His opinion is something she values -- and she always has. _

_ “I still don’t get why you want me to go over your essays,” Jess remarks as he stands and gets a soda out of the fridge. They’re in Luke’s apartment, Rory doing her homework as Jess reads. “They’re already good. You rarely ever make any changes.” _

_ “I do, too,” she argues. “Sometimes my arguments don’t make any sense. You always catch that stuff.” _

_ He opens the soda with a _ pop _ . “This time, it doesn’t need it.” _

_ “You like doing it,” Rory says. “Admit it, you love it.” _

_ He smiles -- that crooked smile she’s so enamoured by, the one that makes her want to kiss him and never stop. “I do,” he murmurs. “I do.” _

_ “Someday you’ll be reading my articles instead.” _

_ “I have no doubt that you’ll get there.” _

_ Rory grins. “And I’ll be reading your manuscripts.” _

_ He cocks an eyebrow. “For what?” _

_ “Your books.” _

_ He shakes his head, but Rory can tell he’s trying to hide a smile. “Put the pom-poms away, Rory,” he says. _

_ “That is never going to happen.” _

-::--::--::--::--::--::--::--::--::--::--::--::--::-

“So? What do you think?” Rory asks nervously. Jess has been reading for twenty minutes now, give or take, and she’s anxious to hear what he thinks. 

He looks up from the manuscript and grins. “It’s really good.”

“Yeah?”  
“I said this summer that this is something only you can write about it,” he says. “And I was right. It’s so incredibly _ you _. And that’s good. It’s so important when it comes to writing.”

Rory laughs shakily. “You’re not just saying that?” 

“Come on. Do you think I would say that if it wasn’t true?”

“No,” she replies. “You wouldn’t.”

He nods in confirmation. “It feels so real. I can _ hear _ your mother accusing me of something.”

“Come on. She likes you well enough now,” Rory scolds him. 

“Did she have enough time to hide her dart board?” 

Rory laughs, and then _ he _laughs, and then --

“I like having you here,” Rory blurts out. “I like having you around.”

Jess leans back in his chair, eyebrow raised. “Oh, yeah?”

“Yeah,” she says, a little flustered. 

But Jess just smiles, and says, “I like being around, too.”

“It works out, then.”

“Seems that way, doesn’t it?”

Rory chuckles softly, and they both fall silent. This feels so familiar -- a moment they’ve repeated over and over throughout the years, but one that never gets old. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess knows he probably should leave, but he’s not ready quite yet. And when he tells Rory that he’s going to be staying a while, and she grins, runs behind the counter and throws her arms around him, it’s all so incredibly worth it. 

  
  


**Notes for the Chapter:**

> pls leave kudos and comment if u don't mind oop


	5. Ace In the Hole

**Summary for the Chapter:**

> Taylor organizes a new festival. Rory and Jess spend more time together.

**Notes for the Chapter:**

> look me in the eyes and tell me taylor wouldn’t do this i DARE YOU  
also i’m sorry this is kinda slow atm but i promise, with all my heart, that you’ve got a storm comin

Jess hasn’t been to a town meeting in a while, and he’s considering skipping, but then Rory tells him that Taylor is trying to organize a new festival, and since Luke isn’t there to bring Taylor down a peg, Jess decides to go. He’s in need of some entertainment, anyway, so what’s the harm?

Rory stops by the diner on her way there, and waits outside for Jess. When he steps out and sees her, he smiles and shakes his head, saying, “You really brought popcorn to this?”

“Of course!” She exclaims. “Taylor has officially lost it. It’s the show of a lifetime.”

“You sound like your mother.”

“I’m channeling her,” Rory explains. “She’s not able to be here, so this is all in her memory.”

Jess laughs. “Okay. But you’re sharing it.”

“Of course.”

-::--::--::--::--::--::--::--::--::--::--::--::--::-

“Our next order of business is installing a new stop sign on the corner of Plum and Peach,” Taylor is saying as Jess and Rory walk in, five minutes late. “Someone keeps putting these  _ obscene  _ stickers on it, with some very derogatory comments about me and my store! We couldn’t get them off, so--”

“We?” Kirk objects. 

“You made us scrub at it for hours,” Andrew adds. 

“--So we need a new one.”

“I’d like to high five whoever’s doing that,” Jess mutters under his breath, and Rory snorts. 

“Do you have something to share with the group?” Taylor asks sternly, glaring daggers at Jess.

“Not at all, teach.”

Rory takes a seat next to Lane, and Jess sits next to her, grabbing some of her popcorn. Taylor glares at Jess for a solid few seconds before launching back into his tirade. “All those in favor of a new stop sign at the corner of Plum and Peach, say ‘aye.’”

“Aye,” the majority of the crowd drones.

Taylor bangs his gavel. “Up next: tourism in Stars Hollow is at an all time low,” he announces. “We’re too boring, too dull, too commonplace. That is why I am proposing an exciting new festival to attract tourists and raise enthusiasm all over town.”

“Here we go,” Rory whispers.

“What’s America’s favorite pastime? The most popular sport in the nation? It’s not baseball, or basketball, or even football. You know what it is?”

“Is it dull town meetings?” Jess calls out. 

“Why are you heckling?” Rory scolds Jess.   
Jess shrugs. “We have to channel Luke and Lorelai together, right?”

“Oh, yes, totally.”

“ _ Anyway _ ,” Taylor says pointedly, “Stars Hollow needs to embrace this fun, whimsical pastime and make it our own. And that, my friends, is why this year we are hosting Stars Hollow’s first--”

“And hopefully last,” Jess mutters.

“Mini golf festival!” 

A murmur spreads across the room, and Taylor bangs his gavel on the podium angrily. “Order, order!” He exclaims. “I know this is exciting, but I can keep you here as long as I need to!”

“Actually, my adult tap class starts at 9:30,” Patty whispers to Taylor.

“Alright, fine. But stop talking so we can finish up!”

Jess snorts. “That’s unlikely,” he mutters to Rory. 

“Jess Mariano, if you don’t have anything nice to say, then don’t say anything at all!”

“Taylor, calm down,” Patty reprimands him, but Taylor waves her off.   
“We have chosen to accept you back into our town--”

“A bad decision, really.”

“So you will treat us all with respect!”

Jess raises his eyebrows. 

“Jess, I swear--”

Rory snickers, and Jess’ heart glows at the sound. He smiles to himself, causing Taylor to roll his eyes, but he continues talking, going on about the price of stamps and how that relates to the festival. Throughout the meeting, Jess sneaks looks at Rory. She looks so  _ happy,  _ which is something he loves to see. 

Once the meeting is wrapped up, Rory walks Jess home. “You were right,” Jess admits. “That was one-hundred percent worth it.”

“Did you have to egg him on so much?” Rory asks, grinning. 

“Of course I did.”

“He was so red by the end. I almost feel bad for him.”

Jess laughs. “I guess asking him which member of the Backstreet Boys he’s related to after using the phrase ‘I want it that way’ was a little too much.”

“He’s going to have you tarred and feathered.”

“Not if I get him first.” Rory elbows him, and Jess gasps in mock offense. “I can’t believe you would do that,” he says, clutching at his heart. 

“You had it coming,” she teases. Jess just shakes his head, but his smile remains. 

There’s a beat of silence before he speaks again. “Do you want to hang out tomorrow?” He asks. 

“Definitely,” Rory replies immediately. 

Jess grins. 

“What did you have in mind?” She asks. 

“Nothing in particular,” Jess admits. “We can go to the festival together, if you want.”

Rory nods. “Yes, I want.”

“Alright, then. It’s a--” He stops himself from saying  _ date.  _ “It’s a plan.”

“‘Night, Jess.”

“Goodnight, Rory,” Jess murmurs. 

She walks off, and Jess exhales deeply. He watches her walk away, but it reminds him of too many painful memories to count -- so he ducks his head and walks inside the diner. Once the door is shut behind him, he leans up against it, trying to clear his head. “She’s just your friend,” he says aloud. “Everything is in the past. Just friends is good.” He hopes that maybe, just maybe, if he says it enough, he’ll believe it. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

So for a while, it’s coffee together and bookstore trips and sleepovers and just wishing hoping praying the feelings go away. It’s “see you tomorrow”s and “catch you later”s and a million other things that make him laugh, that make his heart leap in a way he’s all too familiar with. It’s  _ I know I love you _ and  _ I wish I didn’t. _ Because Jess genuinely likes being her friend, and it works for the time being, and he’s eternally grateful that she’s even letting him in at all. He’s not about to complain. 

So when Rory shows up at the apartment over the diner with a few DVDs and an overnight bag and a “you better have popcorn” as a hello, he lets her in without a second thought. And when she brushes up against him to get to the fridge, and he freezes, and his heart starts beating at a million miles a minute, it’s expected. It’s not a welcome feeling, but it’s expected.   
It can’t escape him that it’s all one-sided. He  _ knows _ that she doesn’t love him back. When their hands brush, she doesn’t feel the sudden electricity that runs through him. She doesn’t fall in love with the way he looks at her when she laughs. It’s unreciprocated, but that isn’t even the worst part -- the worst part is that he doesn’t  _ want _ to love her. He wants all this gone. He wants nothing more than to devote himself to this friendship, because that’s all that it is -- and while he  _ is _ going all in, the guilt he feels for wishing otherwise is threatening to consume him. 

It’s not about Rory, or who she is. It’s about him, about who  _ Jess _ is, and what he’s done. What he’s done to her. He gave up any last chance when he left thirteen years ago. So, seeing her sitting on the couch looking through her movies as he makes some popcorn is more than he ever imagined was possible, even when he first met her. And he promises himself someday, it’ll be enough. 

“Which DVD do you want to watch?” She asks.

“Still haven’t moved out of the early 2000s, huh?” Jess chuckles, looking over his shoulder at her. 

“Hey, at least it’s not VHS.”

“Fair point,” he admits. 

“So?”

“What are the choices?”

“Rear Window, West Side Story, and Dr. Strangelove. All the classics.”

Jess snaps and points at her. “West Side Story.”

“Really?” Rory asks, laughing. “You don’t strike me as a tragic love story kinda guy.”

“Then you’d be wrong,” Jess replies, pouring the popcorn in a big bowl. “As long as they’re good, I’m all for it.”

“How do you feel about Romeo and Juliet?” Rory inquires.    
Jess sits down next to her. “Book or movie?”

“How about both?”

“Hm.” Jess grabs some popcorn and shoves it in his mouth. “The play is amazing. Absolutely incredible. Do you expect me to diss Shakespeare?” 

“And the movie?”

“There’s room for improvement.”

“Hm. And what about Eternal Sunshine of the Spotless Mind?”

“Beautiful film.”

“Wuthering Heights?”

“I must’ve read that a hundred times at least.”

Rory laughs. “Okay, I stand corrected. You truly are a tragic love story guy.”

“Told you.” Their gazes lock. Rory smiles, and Jess smiles back, biting his lip. There’s a moment where neither of them talk -- where Jess starts to hope that maybe--

“Okay, so, West Side Story it is,” Rory says, looking away, effectively ending whatever that moment was. 

“Indeed.”

Once the movie is on, Rory sits back, continuously glancing over at Jess to see what his reaction is to different scenes. She’s excited to see him  _ not _ hiding his emotions like he used to on their movie nights back when they were dating -- no hand over his mouth, no clenched jaw, nothing. Just a smile at the good parts, a sad look on his face at the tragic parts, and his laugh makes her heart glow. 

Jess insists on taking the couch so she can have the big bed. His old bed from his teenage years is currently occupied by Jess’ bags, and he refuses to let her sleep on a leather couch. “And you’re sure?” She says warily. 

“Positive,” Jess assures her. “Now get some sleep.”

Rory nods and climbs into the bed.  _ It smells like Jess, _ she thinks to herself. “Goodnight, Jess.”

He is already asleep. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

The next morning, Rory walks back to the house. She leaves early -- she knows if she’s seen exiting Jess’ apartment in the morning, people will talk. 

Rory grabs a danish on her way out, and walks down the street, taking in the brisk November air. It’s so peaceful -- the streets and sidewalks empty, the sun casting a golden light upon the town. 

Her peaceful walk is interrupted when Taylor comes hurrying towards her. Rory braces herself -- Taylor isn’t who she wants to talk to first thing in the morning. “Rory, I am so glad I caught you,” he says, and Rory knows immediately that there is no escape. 

“Good morning, Taylor,” she says through a forced smile.

“As you know, preparations for the Stars Hollow mini golf festival are underway,” he begins. “And I am putting together a board to help organize it.”

Oh, no. “Taylor, I--”

“And you would be  _ perfect _ for the board!” Taylor exclaims. “Your opinion carries much value in this town, you know?”

Rory grimaces. “I don’t know…”

“Look, I didn’t want to have to bring this up, but you have barely been a part of town functions for a while now,” Taylor says disapprovingly. “You owe us, young lady.”

“Because I haven’t been living here.”

He waves his hand in dismissal. “So, can I expect you at the planning meeting on Wednesday?” 

“I guess so,” Rory says weakly. There’s no point in arguing. 

“That’s great. See you at seven tomorrow.” And with that, Taylor hurries back to his market.

“Wait, is that AM or PM?” She calls after him, but he doesn’t seem to hear her. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess cleans the counter, scrubbing hard at one stain that hasn’t gone away in the past week and a half (and he’s pretty sure it’s been there since he was a teenager), but it’s getting harder to ignore Babette and Miss Patty’s whispering.

It’s been going on for twenty minutes or so now, and they’re insane if they don’t think he can notice. They’ve been shooting not-so-subtle side looks at him, and he has definitely heard his name a few times. He doesn’t know  _ what _ they’re talking about, but it  _ definitely _ concerns him, and honestly, this is getting annoying.

“Alright,” he says, throwing his towel down. “What’s all this about?”

“I don’t know what you’re talking about, honey,” Patty says innocently. 

Jess raises his eyebrows.

“Oh, I can’t lie to that face,” Babette groans. “Come here, sugar.”

Jess frowns, but he walks over and sits at their table all the same. In his defense, it’s been a long day, and there’s only one other customer in the store. (And it’s Kirk. And he’s asleep.) 

“We’ve been talking about you,” Babette admits as if it's some big secret.

Jess shifts, trying to get comfortable. “I know. It’s obvious.”

“No need to be rude,” Patty objects.

“We’re worried about you, Jess,” Babette frets. “I know we didn’t like you in the beginning, but you’ve grown into a smart, strapping young man.”

Patty smirks. “I’ll say.”

“Ooohhhkay,” Jess says, moving away from Patty. “Why are you worried?”

Babette sighs. “I guess there’s no beating around the bush, is there?”

“About what?”

“You’re sticking around for her, aren’t you, sugar?”

“Who?” Jess asks, but the answer is obvious. 

“For Rory, dear. It’s obvious,” Patty adds.

Jess starts to stand up, but Babette pulls him back down onto his chair. “We only want to help you, Jess.”

“I don’t need help.”

“But you do,” she insists. “You’re still hung up on her, huh?”

“No,” Jess says firmly. “Now, I have to get back to work.”

“Oh, get back to what? Your only other customer is Kirk. And I think he’s asleep.”

Jess groans. He doesn’t want to hear this. Look, Babette and Patty are great, but this isn’t any of their business (even if they think  _ everything _ is their business), and he hasn’t told anyone, besides Chris and Matthew, about his feelings for Rory. Next would be Luke, and he’s  _ not _ going to tell Luke, so this conversation is out of the question. 

“We see the way you look at her, sugar,” Babette sighs, shaking her head. 

“Hasn’t changed a bit since you were kids,” Patty adds.    
Jess scoffs. “Jeez, you two are like the old guys in the box seats on the Muppet Show.”

Patty looks at him pitifully. “Using humor as a defense mechanism to hide your feel feelings, huh?”

“What?” Jess replies, puzzled.

“Hey, I took psychology in college.”

“Do you still love her?” Babette asks.

Jess looks away. “No.”

Babette rubs his arm. “It’s easier if you admit it, hon. Then you can go from there.”

As much as Jess hates to admit it, he knows she has a point. Even if he can accept it himself, telling other people that he still loves his ex-girlfriend after thirteen years is so hard to do. But if he does, if he can own this, that might be the first step towards moving on. 

He takes a deep breath, as he is so used to doing, and then he says, “Fine. I still love her.” Babette and Patty look at each other excitedly, but Jess shuts them down. “This isn’t exciting new gossip, okay? Don’t go off and tell East Side Tilly or anything.”

“Oh, God, no,” Patty replies. “She will never catch wind of this.”

“How could you tell?”

Babette clicks her tongue. “Like I said, sugar, it’s the way you look at her.” When Jess remains silent, she hurriedly adds, “but I don’t think she’s noticed.”

Jess nods slightly. After a few beats of silence, he says quickly, “It’s fine. I’m moving on.”

“Are you, though?” Babette asks. Not judgemental, but curious -- actually, genuinely concerned. It’s an odd feeling. He never thought anyone in Stars Hollow would be concerned about him. 

“I’m trying.”

“If it does anything for you, I’m rootin’ for you two kids,” Babette reassures him. “Maybe she’ll come around. Rory’s just been distracted these days.”

Patty nods in agreement. “Just give it time.”

“Thank you,, really, but I don’t need to be comforted,” Jess assures them. “Maybe I...maybe I love her, but it’s not anything new, okay? I’m used to this.”

“That’s just so much sadder!” Patty objects. 

Jess shrugs. “Maybe. But…” When he stands up, this time, they don’t try to stop him. “Can I get anything for you two?” 

“Oh, just some coffee, dear,” Patty replies.

Jess nods, and he gets busy, making and pouring the coffee. He can’t help but think to himself how nice it is that they’re looking out for him. Even if the topic is something he doesn’t like to talk about, they took the time to notice and talk to him about it. He once hated this place, but now? Jess doesn’t think it’s possible. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory collapses in the armchair. “I am  _ exhausted,” _ she complains.

Jess glances up from his book. “What happened to you?”

“I was forced to sit in a board meeting to plan the festival,” she explains, kicking her shoes off. “For three hours we talked windmills and golf clubs. If I see one more ball I’m going to be sick.”

Jess snorts in response. 

“Oh, shut up.”

They’re sitting in the living room of the Gilmore’s house. They arranged to meet there around 1:30, and it’s about fifteen minutes past, but Jess was still there when Rory arrived. 

“Go get some food,” Jess suggests. “You need some fuel if you’ve been there since seven in the morning.”

Rory sighs. “Maybe you’re right. I’ll be right back.”

Jess looks back at his book as she goes to the kitchen, but he can’t focus. He hears what sounds like chip bags falling, and a “Damnit!” 

“So, how’s your writing been going?” Rory asks, coming back from the kitchen with a bag of chips.

“Good,” Jess says simply. “Still doing it.”

Rory sits back down in the armchair. “What have you been working on?” 

Jess shrugs. “Nothing groundbreaking. Bouncing around ideas.”

“Are you going to be the type of author who only publishes every 10 years?” She teases.

Jess laughs. “Maybe. Just waiting for inspiration to hit, I suppose.”

“I’ve been telling you for  _ years _ to write a sequel to The Subsect,” Rory says excitedly. “You should do that!”

Jess shakes his head. “I hate to break your heart like this, but there’s not going to be a sequel.”

“Why not?” Rory pouts.

“I don’t believe in sequels,” he says simply.

Rory gapes at him. “How can you not believe in sequels? The ending was so open!”

“That’s the point, though, isn’t it?” He says. “Not having all the answers?”

She leans forward. “How so?”

“Sometimes stories are just...incomplete. It’s just the way things go.”

Rory sits there for a moment, processing his response. She can’t help but think there’s something behind his answer, some truth he doesn’t want to say. And the way he’s looking at her -- his gaze is intense, familiar…

But, deep down, she knows he’s right, even if she doesn’t want to admit it. Sometimes, there isn’t a satisfying conclusion to a story. Rory and Jess know that better than anyone.

She can’t really call what happened ten years ago  _ closure, _ because it’s not. A broken heart and an “it is what it is” and a closed door is just that -- one door shut with not a single one open. Rory has no real idea of how he feels now, if he’s been with other women, but she’s sure he has -- and that concept leaves her with a bad taste in her mouth. She doesn’t like thinking about Jess with other girls. She doesn’t like it at all. And she knows it isn’t fair of her in the slightest, but it’s the truth. The kind of ugly truth that makes her want to curl up and hide. 

When their eyes meet, Jess knows she’s thinking about the same thing -- what they almost but didn’t fully lose ten years prior. 

It’s that weird kind of moment again -- the soft laugh that tapers off into silence, neither of them willing or able to break the gaze. A gaze filled to the brim with fifteen years of memories that burn and bite. But then Rory looks away, and offers him some chips, and the moment is gone. 

But that type of thing never truly lasts, does it? No matter how much it hurts, nor how much you want it to. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Paris comes by that week, informing Rory that she’s only passing through. They go to the diner for lunch, and Rory is hoping she can get through the meal without any lectures.

But she knows that’s not going to happen.

“I’ve been doing some research on pregnancies in the early thirties,” Paris says right off the bat as they take their seats. 

“Keep it down, would you?” Rory hisses.

Paris rolls her eyes. “You’re so paranoid, Rory. They’ll find out sooner or later.”

“I’d like it to be  _ later,” _ Rory insists.

“Right. Well, as I was saying, I did some research. Pregnancies this late in your life have many more risks. I’m glad you’re not one of my surrogates.”

“Would you get to the point?”

“You  _ have  _ to monitor yourself, Gilmore -- the food you’re eating, how much you’re excersizing, sex--“

_ “Paris,” _ Rory groans.

“You’re at risk of premature labor, preterm birth, preeclampsia -- that’s a complication that affects blood pressure and other organs -- miscarriage--“

“That’s enough,” Rory whispers. “I’ve got it under control.”

Paris looks at Rory as if she’s grown another head. “I am a medical professional, Rory. You should consult  _ me  _ over some Cosmo article on how to look hot while pregnant.”

“I’m not reading Cosmo.”

“That’s what all women say, but then the minute they’re alone? They’re reading the top 10 latest sex positions. Which, by the way, are  _ not _ \--“

“Paris!” Rory turns pink.

“You’ve got to stop getting so flustered over these subjects,” Paris barks. “You’re thirty-two. We’re well past learning about the birds and the bees.”

“So, did you hear that Louise got married?” Rory says loudly, trying to steer the conversation away from this uncomfortable topic.

“Yeah. I give her two months tops before she gets divorced,” Paris replies. And the topic is finished, just like that. 

Paris leaves thirty minutes later, leaving Rory sitting by herself in the diner. She doesn’t see Jess -- she supposes he’s taking some time off -- so she decides to leave, too. 

While she gets flustered when Paris tries to talk about these things, Rory is grateful for Paris’ concern, even if she doubts it’s warranted. She just wishes she could talk to someone else about it -- but Lane is busy and her mother isn’t home yet. And yes, there’s always Jess, but…

_ I’ll tell Logan soon, _ she promises herself.  _ That’s all that matters. _

-::--::--::--::--::--::--::--::--::--::--::--::--::-

The day before the festival, Rory winds up stuck in Miss Patty’s as it thunders outside, rain hitting the roof and creating an admittedly relaxing sound. It makes her sleepy, and because Taylor is droning on and on and on, it’s not hard for her to zone out. 

She knew she’d dug herself a hole by agreeing to help plan the festival, but she’d really hoped that it wouldn’t be so slow and boring. They’ve gone over everything they possibly could, but Taylor won’t let them leave. Everyone else on the board (read: Andrew and Sophie) is listening intently, but Rory is staring out the window, thinking about anything and everything else.

Jess agreed to go to the festival with her -- a stunning difference from when they were kids -- and while she doubts they’ll stay very long, she’s excited. This whole spending-time-with-Jess-thing has proved itself to be very enjoyable, so Rory is intent on being with him as much as she can before he goes back to Philly. Because while they weren’t very close over the last decade, their relationship has evolved to something resembling best friends, and she doesn’t want to give that up for anything. 

Because sometimes, when he was gone, if she let herself think about it too much, she missed Jess so much that it hurt. But it was a different kind of pain than she was used to -- a pain so old and constant that it faded into the background if she was careful enough to let it. 

And now, now that he’s here, it’s a different kind of pain that she’s feeling -- it’s an odd one, one that’s bittersweet and lovely and absolutely terrifying. Because it’s easier when they’re friends, and she can sweep everything else under the rug, but she also misses the old days. The days when they were kids, still figuring the world out for themselves, and that leaves her with a sense of longing that she can’t attach to any specific person. Just a yearning for when things were simpler. She misses that hope she had for the future. She really, really wants it back. 

“Earth to Rory!” 

Rory snaps out of her reverie to see Taylor glaring at her. “Sorry,” she mumbles, straightening herself in her chair.

“Right. As I was saying…” Taylor continues, but Rory can’t stop thinking -- about Jess and Logan and the baby and every little fear she’s harboring. More than anything, she wants her mom back. She needs to get this off her chest before it tears her down to nothing. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

The festival is all day, but Jess and Rory avoid the main crowd and go once the sun has set. It’s been getting colder and colder as the days go by, and Stars Hollow is practically Antarctica at night, but it’s a lot quieter than the day and a whole lot prettier.

They check in -- Babette sits at a small table registering people, and Kirk is behind her, handing out clubs and golf balls to the players.

Once checked in and geared up, they walk to the first hole. The course is set up in the town square. Turns out Andrew has a knack for miniatures, so Taylor therefore decided each hole would be a replication of something iconic in Stars Hollow. The first hole is Taylor’s candy shoppe (“free advertising,” as he’d so humbly put it). Rory goes first, and she hits the ball in a straight line. It misses the hole by a few inches. 

“You’re pretty good at this,” Jess observes, eyes wide.

Rory makes a show of brushing off her shoulders. “My mom would take me a lot when I was a kid. I’ve gotten pretty good.”

“And humble.”

“Shut up and go,” she says, grinning.

Jess sets his ball down and positions himself. Rory watches as he brings the club back, swings, and completely misses the ball. Jess curses under his breath.

“Great job, Noonan,” Rory laughs.

Jess grimaces. “I’m rusty.”

“Sure you are.” Rory takes her turn, easily hitting the ball into the hole. 

“Show off.”

They go throughout the course, passing a mini Luke’s and mini Miss Patty’s, Rory easily getting the ball in the hole in three hits or less each time. Jess, however, struggles -- a fact that Rory finds hilarious. 

“Stop laughing,” he insists when he’s on his sixth hit at hole 14, which is a miniature version of the high school. “Just because you got a hole in one doesn’t give you the right to make fun of me.”

The last hole is a replica of the gazebo. Rory easily finishes in two rounds. “This isn’t funny,” Jess reprimands her when he misses twice. 

“Au contraire. From where I’m standing, it’s hilarious.”

Jess shakes his head, but Rory notices that he’s smiling. 

Afterwards, Rory walks Jess back to the diner. She hugs him goodnight and runs off, and as Jess opens the door, he smiles to himself. Not in a million years did he ever imagine they could be friends like this. And while his whole stay has been a constant reminder of what they’re not, tonight only serves to make him think about what they are. And as he walks up the stairs, he finds that he can’t quite wipe that idiotic grin off his face. 

**Notes for the Chapter:**

> idk why the notes at the bottom from the first chapter won’t go away sigh


	6. Should I Stay or Should I Go?

**Summary for the Chapter:**

> Luke and Lorelai return, and are surprised to see that Jess is still there. Rory catches up with her mother, and Jess avoids opening up to Luke.

**Notes for the Chapter:**

> school is officially killing me i stg. i'm sick now and i have so much work, i'm lucky i was able to finish this sigh

The morning sickness is the worst part. 

Rory can deal with the soon-to-be swollen ankles and back pains, however inconvenient they might be, but spending an hour at the toilet in the morning, every morning, is so much worse. 

_ At least I won’t be by myself anyone, _ Rory thinks to herself. She picks up her mother and Luke today -- in a couple hours she’ll take the Jeep up to Bradley International Airport in Hartford, which is only a good forty to fifty minutes away. She can’t muster the energy to show it right now, but Rory is  _ really _ happy. She’s been missing her mother a lot more than usual these days.

She wants to hear all about the honeymoon, of course -- Rory has a list of questions she wants to ask that’s sitting in her mother’s glove compartment. But, however selfish it may be, she really needs to talk to her mother about the baby. The baby and everything else.

She needs someone to hold her hair back in the mornings. She needs help figuring out why she’s so terrified to tell Jess. Why she can’t get herself to tell Logan. Why she feels so lost and scared. 

Lorelai has done this before, and Rory hasn’t. This is something new, something scary, and while Lorelai may not have all the answers, she has something Rory doesn’t -- experience. Advice. A shoulder to cry on. Anything and everything Rory needs, she knows it all starts with Lorelai -- and that is all she needs. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory watches as people exit the terminal, a never-ending flow of sweatpants and suitcases and passports. Luke and Lorelai’s flight was scheduled to land five minutes ago, so Rory waits by security, sitting in one of the seats with an open book on her lap. She can’t focus, though -- she’s worked herself up for this moment, compiled all the questions she has, imagining seeing her mom for the first time in two weeks -- how they ever managed to stay estranged for months that one time, Rory will never know. She’s barely survived this.

“Rory!” Lorelai calls. Rory grins and immediately pulls herself out of the chair. She runs towards Lorelai, who has ditched Luke and the bags, and throws her arms around her mother as tight as she can. “I missed you!”

“I missed you, too, mom,” Rory says into her mother’s shoulder. When they finally break apart, Luke has caught up with Lorelai, shouldering his bag.    
“What am I, chopped liver?” He grumbles. Rory laughs and hugs him too.

“How was the flight?” Rory asks, stooping to pick up one of her mom’s many bags.

Lorelai groans. “Oh, don’t ask me that. I’m still reeling from the turbulence and the five screaming babies.” 

“Oh, god.”

“You said it, sister,” Lorelai replies. “Now, let’s hit the road. I need some coffee.”

-::--::--::--::--::--::--::--::--::--::--::--::--::-

The ride back gives Rory a chance to update her mother and Luke on the goings-on of Stars Hollow. When she tells them about the mini-golf festival, Luke nearly chokes in surprise.

“Did the whole town decide to completely lose it when we left?” He wonders incredulously.

They go to the diner -- Lorelai says she’s never been more hungry, or more caffeine-deprived, and Luke says he begs to differ. The three of them walk in, and immediately, Luke freezes. Jess is behind the cash register, Sookie leaving with a burger. Luke approaches the counter.

“What’re you still doing here?” He asks, puzzled. 

Jess looks up. “Working,” he says simply. 

Luke frowns. “You were going to leave after a couple of days.”

Jess shrugs. “I decided to stay and help out around here. Didn’t want Caesar to have to handle all the work.”

“I hope you don’t expect me to pay you.”

Jess holds his hands up in surrender. “I’ll just take my tips and leave.”

“Who’s giving you tips?”

Lorelai goes to the counter as well. “I’d like a vat of coffee, good sir,” she says playfully, ignoring the incredulous look on Luke’s face. 

Jess laughs. “No can do. I think I’ve been fired.” He catches Rory’s eye and winks. Rory chuckles softly. Jess tucks his hair behind his ear, and looks away, taking an order from Caesar and bringing it to a table. She watches him, transfixed by his muscled arms and chiseled jaw and --

Rory mentally slaps herself. She assumes it’s just because of pregnancy hormones or something, but the past couple days, she’s been seeing Jess in somewhat of a new light. Not that she didn’t recognize his handsomeness before -- it’s kind of hard  _ not _ to -- but now, it’s all she can think of when she looks at him. His veiny hands, the muscles and tendons in his arms…

_ Stop it, _ she reprimands herself.  _ This isn’t fair of you. _ But then, he catches her eye again, and gestures his head towards Luke and mouths  _ Does no one tip him? _ And then, the thoughts are gone as soon as they came -- 

_ I guess not. Must hurt, _ she mouths back. 

Jess cringes.  _ Ouch. _

Once Lorelai has her coffee, she and Rory walk back to the house arm in arm. And slowly, Rory can feel her hope coming back -- her mom is here. Now, everything can finally fall back into place. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Luke has been back two days, and he still hasn’t made Jess stop working. He grumbles about the tips, yes, but Jess knows Luke appreciates the help, and probably gets a kick out of all the memories it brings up -- he’d be lying if he said he didn’t consider donning a flannel shirt and backwards cap again. 

Jess wipes the counter as Luke counts out change at the register, handing it to the customer. “So, Jess, how was the diner while I was gone?” He asks. 

“It was fine,” Jess says non-committedly. “Had to chase Kirk off a few times, though. He kept saying something about his best hair net?”

Luke groans. “God, I remember that thing.” But then he chuckles. “Seems like it wasn’t anything new.”

“Don’t I know it.”

“You know you didn’t have to stay, right?” Luke asks curiously. “It would’ve been fine.”

Jess shrugs. “Sure. I didn’t mind, though.”

“So, there isn’t another reason you stayed?” Luke inquires, eyebrow raised. 

Jess stops wiping the counter. The way Luke asked, it was like he was insinuating something -- like he knows Jess’ secret. Like he knows that Jess is staying for Rory.

He doesn’t want to talk about it, though, so instead of answering, Jess opens a cabinet and takes a mug out. He pours coffee in it and brings it to Kirk, who is sitting at a table. Luke follows him. “Jess, what’s the problem? It’s just a simple question.”

“Kirk, do you want anything else?” Jess asks instead, ignoring Luke. Kirk says no, so Jess moves on to another table. 

Luke continues to follow him, saying, “You’re staying for her, aren’t you?”

“Do you want a refill?” Jess asks a patron, making an effort to not let his shock of surprise and dread show. How did  _ Luke  _ of all people figure it out? The man cannot read people. 

Luke follows Jess as he goes behind the counter to get the coffee. “There’s nothing to be ashamed of if you are.”

“I’m working, Uncle Luke.”

Luke stays on Jess’ tail, who is fed up. “Stop that.”

“Not until you tell me the truth.”

Jess dodges Luke’s attempt to grab him by the shirt. “Get  _ away.”  _

“Not until you stop acting so secretive,” Luke insists. 

“Go away, you lunatic.”

Luke stops following him, much to Jess’ relief, but he keeps glancing over at Jess, like he’s fragile. Like he thinks Jess is about to break. 

Jokes on him, Jess thinks to himself. That already happened a long time ago. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Having her mother home hasn’t solved all of her problems, but at least there’s someone to hold back her hair now.

“You okay?” Lorelai asks softly, stroking her daughter’s hair as she sits by the toilet.

“Yeah,” Rory says shakily. “It’s just so bad lately.”

“It was for me, too,” Lorelai assures her. “There’s nothing wrong. It just affects some women more than others.”

Rory groans. “Of course it had to be me.”

Lorelai looks at her apologetically. 

Rory takes a shaky breath, trying to soothe herself. She moves next to her mom and leans against the wall. 

“I think I’m ready to talk about it now,” Rory mumbles.

Lorelai smiles softly. “I’m glad.”

Rory closes her eyes. “I’m too scared to tell anyone else,” she says softly. “Besides Lane and Paris. And…” She laughs bitterly. “It’s not even Logan I’m most scared to tell.”

Lorelai’s eyes widen. “Why not?”

“I mean, I’m still worried about telling him,” Rory clarifies. “But there’s only two ways it can go. Either he’ll bail or he’ll say he’ll be involved out of obligation. And he’s not going to want to forfeit everything he has over there for a baby.” 

Lorelai sighs. “And you’re not going to let him give anything up if he offers.”

“Right.”

“Who are you so scared to tell?” Lorelai asks. 

Rory stares down at her lap. She tugs on the sleeves of her sweater absentmindedly, trying to work up the nerve to reveal the answer. “Jess,” she mumbles. 

“Jess.” Lorelai repeats slowly. 

Rory nods, swallowing. “What we have now -- this friendship -- it’s good. We’re at a good place now. We’re getting closer, finally...it took a long time for us to get here, you know?”

“But why would telling him mess that up?”

Rory bites her lip. “I don’t know. I just...I feel like it will. He hates Logan, and I guess he has a good reason to, so…”

Lorelai wants to say it --  _ it’s because he still loves you! _ She knows that the news will shatter Jess, Rory’s not wrong -- but the reason, the reason is so much more than who the father is. It goes so much deeper. 

“I...I’m scared he’ll leave,” Rory realizes. “That when I tell him, he’ll bolt.” And come to think of it, this is what she has been afraid of this whole time -- driving Jess away. Doing or saying the wrong thing and having him leave, again, without saying goodbye. Again. 

“He’s not the same Jess he used to be,” Lorelai admits. “I don’t think skipping town is his go-to move anymore.” But even as she says it, she’s unsure -- even well into her thirties, Lorelai still ended relationships when it felt too real. Who is she to say that Jess officially got rid of his demons?

Rory shakes her head. “He still could.”

“You should worry about telling Logan first,” Lorelai insists. “Not  _ worry, _ really, but focus on that. Then, you go from there.”

Rory takes in what her mother said. “You’re right,” she decides. “That’s what matters most.”

“Here’s what we’re going to do,” Lorelai says. “We’re going to make you a doctor’s appointment for sometime in the next week. I’ll give you two weeks to tell Logan. Then, after that, you can tell Jess. Or anyone else you want to know.”

“Sounds fair,” Rory mumbles. She tucks her hair behind her ear absentmindedly. 

Lorelai wraps her arm around Rory and rubs her arm. “You’re gonna be okay, kid. It’s a little scary now, but it’s okay.”

Rory rests her head on Lorelai’s shoulder. “Thank you, mom.” She closes her eyes. “I missed you.”

“Missed you too, kid.”

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess can’t sleep. 

He’s been lying in bed for hours, checking the clock periodically, which he knows is the worst thing you can do if you’re trying to fall asleep, but he can’t help himself. It’s been four hours -- almost four in the morning -- and he’s wide awake. And all he can think about is Rory. 

He doesn’t understand why it’s so bad  _ now,  _ why it wasn’t this bad before, why every action and look and exchange is  _ charged, _ why he’s thinking about her at night like a lovesick teenager. He’s been here before, and he still doesn’t like it. Not one bit.

Spending the festival with her had been amazing, really -- he loves how she was teasing him and joking and how she hugged him goodnight. 

Jess hates this feeling. This feeling of hopelessness. This fantasizing about what might have been. He’ll daydream the apartment they’d have, books on every surface, light shining through large windows. He imagines every single moment where he could’ve made a different choice -- what if he hadn’t fought with Dean at that party? What if he hadn’t gone to California? What if he’d stayed after he told her he loved her? There are a million words he wishes he could take back, a million things he regrets -- oh, regret. That’s been on his mind a lot these days. 

Because really, Rory is everything to him. She’s flowers growing from cracks in the pavement, she’s a warm fire after a heavy snow, she’s laughter in the rain, she’s a kiss goodnight and a Venice Beach sunset and anything else that’s ever made him happy. He can’t stop torturing himself over her. Because he’s in a good place now, but he can’t help but wonder if he would’ve got this far if he’d stayed with her. He thinks that maybe he would. 

It’s stupid to think about, because there is now way to change the past, and Jess wants to just stop thinking about this all together. But it’s been hours, and he’s tired but also not, and if he lies there any longer he’s positive he’ll go insane. He knows what he needs to do -- something he should have done a long time ago.

So, Jess pulls himself out of bed, trades his sweatpants for some jeans, runs down the stairs, and starts walking towards the Gilmore house. 

He’s anxious -- it’s the same type of feeling he gets whenever he opens up, admits to something he’d much rather pretend didn’t exist. But it’s been a long time coming. He has to give what is owed.

The crunching of the gravel under his boots as he walks up to the door is familiar, and the slight creak of the second step only serves to remind him of the past. And when he knocks on the door, he is endlessly hoping that the right person opens it -- he doesn’t want anyone else involved. 

The door swings open a minute or so later, and Jess can breathe. Luke stands there, a puzzled (bordering on irritated) expression on his face. “Jess? What are you doing here? It’s four in the morning.”

Jess swallows. He’s worked himself up, now, on his way over. And now, all his emotions is at the top, threatening to spill all at once. “I’m ready to talk,” he manages to say, his voice hoarse.

Luke’s expression softens at Jess’ voice. “About what?” He asks, even if he already knows.

“Rory,” is all Jess can say.

“Still?” Luke’s voice isn’t harsh, isn’t judgemental, isn’t anything that makes Jess want to tear his own heart out in shame -- rather, it’s almost uncharacteristically gentle, understanding, a side of Luke that is rarely seen. 

Jess nods. His throat is dry, he notices. 

“Lucky for you, she’s crashing at Lane’s tonight,” Luke replies. “Come on in.”

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess collapses in one of the chairs at the kitchen table, rubbing the exhaustion from his eyes. Of course,  _ now _ he’s tired.

“I’d make you some coffee, but Lorelai is like a bloodhound when it comes to hearing the coffee maker,” Luke explains, taking a seat as well.

“It’s fine,” Jess says. “I...I’m sorry for this,” he says lamely.

Luke dismisses his apology. “It’s okay, really. It’s preferable to chasing you around the diner.” Luke notices Jess’ leg bouncing, but doesn’t say anything about it.

Jesus chuckles. “Probably.”

“So, you’re still in love with Rory, huh?” Luke says awkwardly.

Jess looks away and nods firmly. “Yep.”

“Since you last told her?”

“Yep.”

“I had a feeling,” Luke says. Jess raises an eyebrow in disbelief. “Okay, fine, Lorelai had a feeling, but I agree with her.”

Jess’ jaw clenches, and Luke thinks he made a mistake mentioning Lorelai, but then Jess just lets out a deep sigh and says, “She’s perceptive, that Lorelai.”

“She can be.”

“It’s stupid. And embarrassing,” Jess says. “Being in love with a girl who I haven’t dated in thirteen years.”  _ And I loved her before then,  _ Jess thinks to himself.

“Look who you’re talking to.”

Jess chuckles, but he quickly sobers up. “I can’t get myself to leave,” he mumbles. “After everything, all the times I’ve left, I just...can’t.”

“Because of her?” Luke guesses.

Jess nods. “Because of her.”

“Why not just take your shot? Tell her how you feel?”

Jess laughs bitterly. “I’ve done that before. Never ends well.”

“You both are at very different places than you were back then,” Luke argues. “You’re not just a scared teenager anymore.”

“I feel like it sometimes.” 

“We all do.” Luke draws circles on the table with his finger as he speaks. “But you’re different now, Jess. She’s different, too.”

Jess bites his lip. “She doesn’t feel the same way.”

“How do you know?”

“I just do,” Jess replies. “And I don’t want to put myself out on a limb like that and risk ruining our friendship.”

“How much of a friendship can it be if you’re not telling the truth?” Luke asks. When Jess stays silent, Luke hits the table with his figure in triumph. “And  _ that, _ my nephew, is the problem.”

“We don’t talk about relationships,” Jess explains. “It’s too weird. It’s too much. We’re better off ignoring that part of our lives.”

Luke remains unconvinced. “But you’re friends.” 

“We’re still exes, too,” Jess points out. “There’s still a lot of history there that we’re both ignoring. And it seems to be going fine. We’re getting closer, we really are.”

Luke frowns. “How are you getting closer if there’s a huge roadblock between you two?”

“We’ve been spending a lot of time together. We went to the festival together--“

“Oh, you mean that insanity plea Taylor put on while I was gone?”

“We have movie nights, walk around town, eat at the diner, sleepovers -- friend stuff.”

_ “Adult _ sleepovers?”

Jess gives Luke a look. “How old are you again? Five?”

“Is that what you want?”

“It doesn’t matter what I want,” Jess says firmly. “I need to put these feelings behind me.”

“You don’t have closure,” Luke points out. “Can’t do that without closure.”

“I think her not feeling the same way is closure enough.”

Luke shakes his head. “No. As long as you aren’t being honest with her, and she hasn’t said she doesn’t love you back, then it’s not closure.”

Jess is silent for a moment (or several). When he finally speaks, his voice is subdued and hoarse. “I’ve been trying so long and so hard to put this all behind me,” he chokes out. “And I thought I was good, you know? I thought...I thought I could ignore how I felt. And then I come here, and I see her, and...I was wrong. No matter how hard I try…” He trails off.

Luke sighs. “I’m sorry, Jess. I really am.”

“There’s no end to this, is there?” Jess wonders aloud. “I thought I’d come to terms with this. That I’d always love her, and only her, and I’d be fine. I’d be single, sure, but fine. I’ve been a loner before. And now...I’m not so sure I can still believe that.”

“Why not?” Luke’s voice is soft, now, quiet -- he’s really worried for Jess. He really feels for him. 

Jess tales a deep breath, working himself up to this. To tell Luke everything, every little ache and pain in every nook and cranny of his heart. Because he can’t keep this to himself anymore. He can’t. “I’ve made a lot of mistakes in my life,” he begins. “I was in a really bad place when I met her. And yeah, I put that all behind me, but…” He swallows. “I hurt her. I was...I was lost and scared and didn’t know where to go after…” He trails off guiltily.

Luke dismisses it with a wave of his hand. “After I kicked you out. It’s fine.”

Jess sighs. “I couldn’t face her. I hid  _ everything  _ from her -- getting kicked out of school, my dad visiting, every little fear and insecurity I had...I was never able to tell her. And then, it was too late. I thought...I thought I was doing both of us a favor,” he chokes out. “But somewhere deep down, I knew I wasn’t.”

Luke grabs the tissue box from the counter and puts it in front of Jess. He looks gratefully at his uncle before continuing.

“I think I punished myself for that. I never forgave myself. It tortured me  _ constantly, _ and when my mother told me you had my car, I knew that by coming here I was entering enemy territory. And part of me...part of me wanted to apologize to her. To try to...to fix what I broke. I would’ve done anything to do that, if I wasn’t so scared.” He shakes his head. “I told myself I would avoid her at all costs. That maybe that would save her from hurt. But I kept seeing her around, and it was getting harder and harder not to talk to her…”

“You did eventually.”

Jess scoffs. “I almost didn’t. But I saw the money you left me, and I was going to go thank you, or something...and then I saw her.” He swallows again. “I  _ had  _ to talk to her. I had it in my head I was going to tell her I loved her. No matter how hard it was...and it was hard. But I did it.”

“Then you ran,” Luke recalls.

“Drove.”

“Right.”

Jess sighs. “I was too scared to see her reaction. Or lack thereof. So…” He trails off, trying to fight off the tears that are threatening to spill. Luke nudges the tissue box towards him. Jess takes one and blows his nose before he speaks.

“And then...I don’t know. Asking her to run away with me, getting shot down...I know I was putting her on the spot, and it wasn’t right, but I just…”

“Just because she said no doesn’t mean she didn’t want to be with you,” Luke says suddenly.

Jess stares at him in confusion. “What?”

“Your heart was in the right place, Jess, but…” He pauses. “Rory was happy at Yale. She liked where she was. You spilling your heart out and asking her to run away with you, however romantic that may be, gives off a kind of ‘all or nothing vibe,’” Luke explains. “Just because she said no doesn’t mean she didn’t love you. She was flustered and you caught her off guard, and she couldn’t really  _ think.”  _

“Just another thing I regret,” Jess mutters.

“Go on.”

“Writing  _ The Subsect... _ it was all because of her,” he says, his voice gravelly once more. “I had to show her. Tell her. See her reaction. I owed it all to her. I still do. And it’s like…”

“Like what?”

“It’s like every time I see her, I start hoping that maybe we can make it work. That she’ll love me back. But something always happens to shut me down.”

“Like Logan,” Luke suggests. 

“Like Logan,” Jess confirms. 

“But what about now?” Luke asks. “What shut you down this time?” When Jess doesn’t answer, Luke smiles. “See? Maybe it’s not so crazy to try.”

Jess shakes his head. “No.”

“Why not? Give me  _ one reason _ why--“

“Because I can’t do that to her!” Jess exclaims suddenly. “And I can’t risk getting my heart broken all over again! I’ve done it before, and I’m not making that mistake again! I have spent  _ years _ picking apart every moment I have ever had with her and wondering what I could have done differently, torturing myself over and over about why I didn’t open up and why I left and a million other things. Why I didn’t save us the heartache. I do not _ need _ a new ‘what if.’” His voice is fragile, close to breaking -- just like he’s felt for so long. “All the pain -- I had it under control. But I…I  _ want  _ her. I want her to love me back. And all of that just makes me feel exactly like I did fourteen years ago when she was with Dean.” He is fighting off tears, trying desperately not to break down.

Luke sits there, a little stunned, processing everything Jess said. He opens his mouth, then closes it, trying to figure out the right thing to say. “I didn’t know it went that deep,” Luke says finally. 

Jess sniffs. “Neither did I.”

They’re silent for a few moments. Jess wipes at his eyes, trying to calm himself down. 

“You don’t have any new self help books, do you?” Jess asks weakly.

Luke shakes his head. “There’s no easy fix to this, Jess.”

Jess nods slowly. “Do you think I should leave?” He asks. 

“Do you want to?”

“No,” Jess says quietly. “I don’t. I just know I should.”

They’re quiet for a moment. 

“Fuck it,” Luke says suddenly. He gets up and turns on the coffee machine. “It’s too early for alcohol, so this is the best I got.”

“I’ll take it.”

They hear some footsteps, and soon, Lorelai is in the doorway, bleary-eyed and tired. 

“What’s going on in here?” She asks. “You’re making coffee? And why is Jess here? Am I hallucinating?”

Jess turns away. He doesn’t want Lorelai to see him like this -- nearly crying, broken-hearted, rock bottom. But even tired, Lorelai Gilmore is shrewd. She sits down in the vacant chair, watching Jess, trying to get a read on the situation. “Seriously, why are you here? It’s four AM.”

Jess stares down at his lap. “I, uh…”

“We needed to discuss how he handled running the diner while we were away,” Luke cuts in. Jess shoots him a grateful look. 

“Oh. Okay,” Lorelai replies, not quite believing them. “Can you pour me a cup?”

“I’m on it.”

Jess stands up. “I’m going to head back,” he says. “Thank you, Luke.” Luke nods.

On his way back to the diner, Jess can’t help but notice the slight relief he feels after getting it all out. And while the weight is still there, it’s lessened, and that’s more than he ever expected. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory sits cross-legged on the floor of the living room, going through a box that’s at least 32 years old, labeled  _ Rory. _ Inside are photos, stuffed animals, and other things Lorelai saved from Rory’s infancy.

She goes through the photos, smiling to herself as she goes. 

Then, there’s a baby book -- Rory opens it.  _ First word: mama. She could hold her head up from birth!  _ And a bunch of other little notes. 

There’s this overwhelming sense of  _ connectedness _ from the past to the present. From then to now. And looking through the photos and home videos and everything in between, Rory has never felt closer to her mother than she does now. 

  
  


**Notes for the Chapter:**

> can't wait to get to the Good Stuff


	7. Wasn’t Born to Follow

**Summary for the Chapter:**

> Jess and Rory really open up to each other for the first time in a while.

**Notes for the Chapter:**

> i’m rly excited to get to one certain chapter so i gotta push thru the next few anyway enjoy !!

After talking to Luke, Jess doesn’t know where to go. All of his feelings are at the front of his mind, impossible to ignore, and he’s not sure he can stomach it. Getting it all off his chest was relieving, yes, but now what? Where does he go from here?

Tonight, he goes to the lake.

It’s five in the morning and it’s mid-November, so the sun isn’t up yet. It’s still dark, and a little chilly, but Jess is tired and upset and heartsick -- and the lake has always been a place for him to go when he feels like this. 

He sits down on the bridge, staring at the water below. He’s been here before, and he hates that -- sitting in the same spot he did years ago after getting into a car crash with Rory. He hasn’t smoked in over a decade, but he would really appreciate one right now. 

_ I didn’t know it went that deep, _Luke had said. 

_ Neither did I. _

And that’s what it comes down to, the crux of it all -- Jess hasn’t let himself really _ feel _ this before. He’s always stopped himself before it got to this point. Opening up and feeling everything come to the front of his mind is both a blessing and a curse. And right now, it feels like the worst curse of them all.

Jess is still in love with Rory, and at the end of the day, that is what kills him. The pain that accompanies this longing, this _ yearning _\-- this never ending I-wish-you-would. 

He misses everything about her. He misses kissing her, gazing at her, knowing she is happy because of him. He’s been missing this for thirteen years.

He wants to cry, he wants to tear away his walls and break down -- but he won’t. He _ can’t. _He cannot allow himself to let down his guard any further. It’s only going to break him more. He sniffs, fighting off his tears. 

“Can’t sleep?”

Jess looks up to see Rory standing above him, a gentle smile on her face. It’s as if he summoned her.

He shakes his head. “Nope.”

“Me neither.”

Jess smiles and gestures for her to sit down. She does so, letting her legs dangle over the water. Jess wipes his eyes. “What’s keeping you up?” She asks softly. 

Jess shrugs. “This and that.” Pause. “You?”

“Same here.” She exhales slowly. “Got a lot on my mind tonight.”

He nods, not trusting himself to speak any further. She sighs again. 

“You okay?” She asks, glancing over at him worriedly. Jess had hoped they could avoid discussing him being on the verge of tears, but this is Rory -- and she cares about him. For some reason, some godforsaken reason, she cares about him still. That thought only makes it more tempting to break down. 

He clears his throat. “Doin’ great.”

“You want to talk about it?”

He shakes his head. 

“Oh. Well, that’s okay, too.” Beat of silence. “Haven’t been out here in a while,” she says suddenly. 

“Me neither.”

Jess knows what they’re both thinking about -- it doesn’t take a genius to figure it out. The same bridge fourteen years ago, a confession, a tender gaze -- the start of something that Jess has yet to get over. 

“Kinda missed it,” she continues, staring ahead of her. “It’s a good place to clear your head.”

“Amen,” he manages to say. 

Rory chuckles softly. “Can’t believe how long it’s been since we were last here together.”

Jess’ jaw tightens. “Yeah.”

“I mean, it’s so weird to think about,” she continues, taking his short reply as encouragement to keep going. “That, what, fourteen years ago, we were both here?” She half-laughs. “Really takes you back.”

“Mhm.”

“We’ve had some times here, huh? I mean, the dance marathon...god, it feels so long ago. Can you believe--”

“Stop!” Jess suddenly explains. “Just stop! I don’t want to…” He trails off, immediately regretting his outburst when he sees her flinch from the corner of his eye. “Sorry,” he murmurs. “I’m just…”

“It’s okay,” she says, a puzzled look on her face. “It’s okay.”

Jess nods, his jaw still tight. He doesn’t dare look at her. It’s only going to hurt him more. 

“Hey.” Rory places her hand on his arm, and he’s forced to glance over at her. She looks concerned, more concerned than she has any right to be. “I’m...you can always come to me,” she says, “whenever you need it. You’ve always helping me get back on my feet. And I can be that person for you, too.” Pause. “If you want.”

Jess presses his lips together before he replies. “Thank you, Rory,” he says. “But I’m okay. Just tired.”

She knows he’s hiding something, but she doesn’t push -- instead, she smiles and brushes his hair out of his face. “Okay. I’ll give you some space.”

They’re both building up their walls, hiding in plain sight, dancing around every question, around each other. And when Rory stands up, Jess only feels farther apart from her. “Feel better, Jess,” she murmurs.

He nods. He’s tempted -- oh, he’s so tempted -- but the words _ I love you _ die on his lips. He decides on a “I’ll see you later,” and she smiles and leaves. 

Jess sits there a little while longer, but his head is anything but clear. He needs to leave. But all he has is a reason to stay. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory probably should’ve seen this coming. 

She knows it probably doesn’t mean anything, but she can’t stop thinking about it. And, yes, her suggestive thoughts about Jess recently mean this shouldn’t surprise her...but still. Having dreams about _ it _ is a whole other ballpark.   
She went to the lake to clear her head, but Jess had been there, as if she had summoned him. So, now, she sits with Lorelai in the gazebo. It’s the afternoon, and they just had a large meal at the inn, and Luke has monopolized the living room, so here they sit. 

“What’s up with you?” Lorelai asks, eyeing Rory warily. 

“I had a dream,” Rory replies. She’s been acting awkward and weird, so she can’t blame her mom for asking. 

“What about?” Lorelai asks.   
Rory shifts uncomfortably. “I don’t know if I should say.” _ Or if I want to. _

Lorelai furrows her brow in confusion. “How bad could it possibly be that you don’t want to talk about it?” When Rory doesn’t answer, Lorelai takes that as her cue to continue. “How problematic was it? Would twitter be angry? If it would upset Emma Thompson, I don’t want to hear it.”

Rory stares down at her shoes. “It was about Jess,” she mumbles. 

“Jess?” Lorelai exclaims. 

Rory shoots her a glare. “You could’ve said that quieter, but yes, it was about Jess.”

“Was it..._ that _ kind of dream?” 

“Yes,” Rory admits. She can feel her face turning pink. “I thought you could analyze it, maybe. Only if it’s a good answer.”

“Maybe you just want to sleep with him,” Lorelai suggests.

“No. Try again.”

“Hey, you don’t get to reject my analysis if I can never reject yours.”

“Try. Again.”

Lorelai hesitates. “It’s a tough one,” she admits. 

Rory sighs. “It’s probably just pregnancy hormones, right?” She asks desperately. “It’s only been this past week that I’ve been...noticing...things...about him…” She clears her throat. “And this is the first dream. If that means anything.”

“It’s very possible it’s the hormones,” Lorelai agrees. “And you’re sure there’s no romantic feelings there whatsoever?”

Rory nods. “None.”

“Then it’s probably just the hormones,” Lorelai concludes, and Rory can breathe again. “That, and maybe you’re lonely? After everything with Logan and...Petey?”

“Paul,” Rory corrects her. “And, yeah. That makes sense.”

“What were you so worried about?”

Rory bites her lip. “I don’t know.” And that’s the truth -- she doesn’t know why the dream freaked her out so much. Maybe it was just because it was _ Jess _ in the dream, her ex, her friend -- and while that makes sense, it also brings up more questions. An endless list of questions.

Lorelai frowns. “What exactly was the context of this dream?”

“Nothing out of the ordinary,” Rory says awkwardly. “Just...him, and me, in the apartment above the diner…but I woke up before anything actually...happened...” She trails off. She does _ not _want to get into details. It’s too much. Thinking about kissing Jess, her hands in his hair, his body heavy on hers-- 

Lorelai nods thoughtfully. “It’s probably just because he’s here. Your brain just inserted him into the dream because you’ve been seeing him around.”

“Yeah,” Rory says shakily. “Yeah, you’re probably right.” 

But Rory is still unsure -- a feeling she’s used to when it comes to Jess. So she tells her mother about that morning, after she had the dream, finding Jess at the lake...Lorelai listens intently, thoughtfully, unsurprised when Rory tells her of his outburst.

“He probably just doesn’t like to think about the past,” Lorelai says. “That was a very troubling time for him.”

Rory figures that’s all it is. It’s so much easier that way -- none of it having any other meaning than what she _ wants _ it to. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess sits on the couch with Luke while the television plays, but he isn’t paying attention. Rory and Lorelai are out, doing god knows what, so the house is fairly quiet. It’s a rare occurrence, but a relaxing one to say the least. 

“You haven’t been hanging out much with Rory these past few days,” Luke notes suddenly. “Anything up with that?”

“No,” Jess snaps immediately. 

Luke raises an eyebrow.

“Sorry,” Jess mutters. “Reflex.”

“It’s okay,” Luke reassures him. “But something is obviously still up with you, Jess. You need to work this out. Soon.”

“Well, maybe I can’t deal with it right now, or whatever,” Jess grumbles.

Luke shifts so he can face Jess. “Rory?”

Jess nods grimly.

“Are you avoiding her?”

Jess exhales slowly. “Maybe. I don’t know.”

“Talk to me,” Luke offers.

Jess wraps his arms around himself and bites his lip. When he doesn’t say anything, Luke sighs. “I once told you that I was always here,” he begins. “And that...that still applies, Jess.” Pause. “If you’ll let it.”

Jess swallows. Every time he opens himself up, it’s a challenge. And, yes, he loves Luke, and he trusts him -- but it’s still difficult. He doesn’t have to worry about reciprocation here -- Luke will listen and do his best to help -- and yet, something is still trying to hold him back. “I went to the lake the other night after we talked,” he says shakily. “I was trying to...I don’t know, clear my head, but then…” He swallows again. “Rory showed up.”

“Oof.”

“I was…” He won’t talk about the almost-crying -- that’s too much. Instead, he closes his eyes, and continues. “I was sitting there, and she sat down next to me, and…” He turns to face Luke. “Do you remember that dance marathon? When I was living here?”

Luke nods.

“Well...after Dean broke up with Rory, I found her at the lake. Same exact spot.” He lets out a deep breath. “And she started talking about it, how long ago it was, and other things. And I just...snapped at her.”

“Why?”

“It was too much. Of _ course _ I was thinking about that night -- how couldn’t I? But that night...that was the night…” She clears his throat. “That was the night we...”

Luke shakes his head. “And it bothered you to hear her talking about it.”

“How could it not?” Jess runs his hand down his chin. “I can’t hear her talking about it. It hurts too much. I just want this to go away.” His voice cracks on the world _ away. _

“Jess…”

“I don’t really want to talk about this anymore,” Jess says quietly. “I don’t really feel like crying or anything. Which is where we’re headed.”

“That’s okay,” Luke reassures him, but sounding a little rushed. He probably doesn’t want to see Jess cry -- which Jess understands. “Take your time.”

Jess nods. “Thank you.”

“Anytime.”

He wipes his eyes with the back of his hand. He can’t escape these feelings, no matter where he goes. Maybe that means he should leave, he thinks. Maybe that’s a sign. 

“How much longer do you think you’re going to be staying in Stars Hollow?” Luke asks, as if he can read Jess’ thoughts.

Jess shrugs. “Dunno.”

“No pressing matters over at Truncheon?”

He shakes his head. “Nope.”

“Stay for the holidays,” Luke suggests. “We’ve got some events coming up, and I have to admit...it’s nice having you helping out at the diner,” he finishes bashfully.

“Getting soft on me?” Jess teases.  
“It happens when you get old.”

Jess leans back. “What events?” Luke hesitates, and Jess knows _ exactly _ what event he means. “The dance marathon,” he says, answering his own question. 

Luke nods in confirmation. “I mean...it could be fun to stay for it.”

“We’ll see,” Jess sighs. “But Doula likes that I’m around, so...I’ll consider it.”

“Good.”

Jess smiles. He feels a little bit better -- bit by bit, he’s healing. And maybe it feels like it all goes away whenever he sees Rory, he knows he’s getting better. Mending himself a little at a time.

Maybe, someday, this won’t hurt so much. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

After his small outburst at the lake, Rory worries that he’d be completely closed up all over again -- so she’s relieved when that isn’t the case. They both seem to want to move past it. So, Rory spends the better part of the week with Jess. 

Jess meets her at Weston’s after Doula’s dance recital, and she laughs to see that he’s out of breath when he walks through the door.

“What, did you run here?” She laughs. 

Jess shrugs. “Didn’t want to be late.”

Rory’s heart twinges at the smile he gives her. Despite what everyone used to say about him, Jess is a good guy -- in a way that makes her feel bittersweet. 

“So, you still living above Truncheon?” Rory asks once he’s sat down, taking a sip from her coffee. 

Jess shakes his head. “Not anymore. I actually found this apartment about five years ago -- it’s a nice one, too. It’s only a few blocks away from Truncheon, and it’s reasonably priced, so I’m able to afford rent myself.”

“Bachelor pad?” Rory asks playfully, but she regrets it as soon as the words leave her mouth. Jess goes quiet, and his jaw tenses, and Rory worries that he’ll get angry or yell or shut off completely -- but then he does something even more surprising.

He smiles. “I wouldn’t say that,” he chuckles. “I...haven’t dated much these past ten years.”

“No?” His revelation, oddly, makes Rory feel relieved.   
“No,” he confirms.

“Why not?” This moment is fragile, and Rory is terrified of saying the wrong thing -- but then again, this is _ Jess. _Mature Jess, confident Jess, a Jess who is opening up to her. It seems almost silly, now, that she thought he would bolt -- because here he is, talking casually about his romantic life (or lack thereof, she supposes) without any hint of wanting to run. 

Jess shrugs. “Just haven’t met anybody,” he replies. “I’ve gone on some dates, but they don’t go anywhere. I went out with this one girl -- she burst into tears when I told her I was an author.”

Rory laughs. “Why?”

“No clue, but it’s safe to say that’s not my type.”

Rory shakes her head. “That’s a shame.”

“A lot of unsuccessful dates,” he says. “Never more than one night, really.”

“So just one-night stands?” She asks, realizing right after she says it that it’s out of line. But Jess doesn’t seem to think that.

Instead, he says, “Are you slutshaming me?” The corner of his mouth turns up. 

“Oh, definitely.”

“So, what about you? Leaving behind a trail of broken hearts?” Jess asks jokingly. When Rory hesitates, and doesn’t answer, he immediately says, “Did I do something, or…?” His voice soft and worried. Rory softens at that.   
“No, no, you didn’t. It’s just…” she swallows. “My dating life in the last ten years is not something I’m proud of.” 

“We can talk about something else if you want,” he offers gently. 

“It’s okay,” Rory assures him. “There wasn’t really anyone for a while. I guess Luke told you Logan proposed to me when I graduated?”

Jess nods. “And that you turned him down. Cold. I heard it was vicious,” he teases. 

Rory snorts. “Not exactly. But, I dated this guy, Paul for a couple years.”

“Is that P?” Jess asks, recalling seeing her write “break up with P” on a post-it that summer.

Rory nods. “Yeah. We broke up this month.”

“I’m sorry.”

“No, don’t be. It…it didn’t fit. And…” Rory bites her lip. She doesn’t know how real she wants to get here, how much she wants to tell him -- she is not proud of the way she treated Paul, not in the slightest, and she’s sure Jess wouldn’t be, either. But the way he’s looking at her...gentle, curious, concerned…”I wasn’t that great to him.”

Jess nods slowly. Rory is scared to tell him, scared to see his reaction -- but oh, god, she wants to tell him. She wants to be open with him like he was with her. Rory knows how hard it is for him -- she owes him this much. “I cheated on him,” she manages to say. She avoids looking at Jess as she speaks. “I cheated on him with Logan.” It comes out hoarse, and she sniffs, trying not to break down in front of him. 

“Rory…”

She sniffs, shaking her head. His voice is too gentle, too tender. She doesn’t deserve that, not after what she’s just confessed. “Does that...does that make you hate me?”

“No,” Jess says firmly. She peeks up at him -- there isn’t a single trace of hatred or disgust on his face. “You’ve made mistakes. We all do. The important thing is that you learn from them, right?”

“But I’ve done it before,” Rory replies guilty. “I was with Dean when he was married.”

“That doesn’t make you a bad person,” Jess insists. “Good people do bad things. I know you, Rory,” he says, and the tenderness in his voice sends chills down her back. “Sometimes you lose yourself, but you always find your way back.”

He’s right. Rory knows he’s right, and the affairs with Dean and Logan both happened at times in her life where she felt lost and alone and was still reeling from something else. She’s done the same to Jess, she realizes guiltily. Rory wonders if he’s thinking about that, too. 

Truth be told, she hasn’t given that day enough thought. She wanted to put it behind her, wanted to focus on Logan, forget how she hurt Jess. Because she _ did _ hurt him. She led him on, not realizing it at first, unaware that he still loved her -- she’s never really been good at reading people, but she thought she could read him. She had realized it too late -- when he kissed her. When she saw the heartbroken look on his face that he was struggling to hide for her benefit.

“I’m not with Paul anymore, so that’s all over. And I don’t intend to do it again.”

Jess nods. Rory can tell he has something he wants to ask her, but he doesn’t. Instead, he says, “Then don’t beat yourself up over it.”

“Why are you being so nice to me?” Rory asks quietly. “After...everything?”

_ Everything _is such a loaded word. Everything. Their entire history, maybe, or perhaps only what she just said. 

Jess frowns. “Why shouldn’t I be?” 

“I’ve hurt so many people,” Rory mumbles. “I can’t seem to stop.”

“I felt like that once,” Jess says. “But it goes away with time.”

Rory sighs. “I’m already thirty-two. I don’t _ have _ time.”

“Hey.” Jess reaches out and puts his hand on hers. “It’s okay.”

“But--“

“You are not your mistakes, Rory.” Jess squeezes her hand. “You’re so much more than that.” 

He’s not letting her off the hook, and for that she’s grateful -- the people who love her have always dismissed anything bad she’s done -- but here Jess is, acknowledging that she’s done bad things, but without judgement. He still knows her -- and he believes in her. He truly believes that she will learn from this. She wishes she could have the same faith in herself that he does. _ He doesn’t know that you’re pregnant, _ she thinks to herself. _ He doesn’t know that you actually, really messed up. _

Instead, she says, “Thank you, Jess.” She finds herself smiling. 

He can’t help but smile back. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

As time passes, Rory builds her way up to telling Logan. She’s told Lorelai, Lane, and Paris so far, so who else could she tell? She decides on Luke.

He’s surprised at first -- almost thinks she’s joking, but then he sees the look on her face, and he knows she’s serious.

“Did you know about this?” He asks Lorelai, who is lounging in the armchair eating a pop tart. 

“Mmph,” she confirms, her mouth full. 

Luke blinks a few times, dumbfounded. “Who…”

“Logan.”

“Oh,” he says. “Oh.” He sits there for a little while longer, and Rory catches Lorelai’s eye -- her mother is making an effort to keep herself from laughing. “You should be sitting!” Luke suddenly exclaims.

Rory frowns. “What?”

“Sit! Rest! Relax!” Luke sounds almost frazzled. “You’re pregnant!”

Lorelai snorts. “Do what the man says. He’s going to have a conniption if you don’t.”

Rory slowly sits down on the couch, eyebrows raised at Luke. But she’s relieved -- he cares about her, he’s worried for her, he’s not shaming her for it -- and that’s all she needs. _ One step closer, _ she tells herself. _ One step closer. _

-::--::--::--::--::--::--::--::--::--::--::--::--::-

With everything going on, it’s been hard for Rory to focus on writing her book. But she has about seven chapters done, and she’s ready to get into her Chilton years. To prepare, she has her yearbooks out, old issues of the Franklin, and her old blazer is on her bed. It feels odd to look back on these days -- her first day, her rivalry with Paris, and everything else from her sophomore year that feels so long ago. 

And, of course, there’s Dean.

It was weird, seeing him after all those years -- but the thing is, with Dean, she has no hang ups. She used to, once upon a time, but now? She looks at him and can look back fondly on the old days with barely any regrets -- the only thing she still cringes at is the affair -- and it’s a good feeling. She doesn’t have that with Jess or Logan. Not yet, at least. 

But as she writes, she thinks back to what Jess said to her that one day in Weston’s -- “Don’t dance around the truth because you don’t want to offend,” he had said. “Look at all the people in your life, and reflect.”

And although there are so many good memories associated with Dean -- he was her first everything, and there’s an attachment there that will never truly fade, even if the feelings have -- for the first time, she allows herself to think of the negative. Because while there was good, there was also bad. It took her a long time to be able to admit that.

Rory loved Dean, she really did, and he loved her. It’s hard to allow herself to think about the bad, but she forces herself to. She may grow warm when she thinks about going to the dance with him, but it hurts a little when she recalls the first time he broke up with her. How she’d been too afraid to say she loved him back, how he’d gone in with these expectations -- how much she hurt in the aftermath.

She smiles when she recalls their first kiss, but remembering his anger and outbursts wipes it off. She’s told him he was the best boyfriend, but now, she finds herself wondering if that was really true. 

**Notes for the Chapter:**

> always feel free to comment ur thoughts. feedback is always welcome.  
also this is making up for all the lack of communication in the show lol


	8. Baby, You Make Me Crazy

**Summary for the Chapter:**

> Lorelai takes Rory to her doctor’s appointment. Jess runs into an old flame.

**Notes for the Chapter:**

> i love how motivated i am to write this it’s so refreshing — thank u guys for reading!!!

Lorelai drives Rory up to Hartford to see the doctor.

It’s a sunny day, which is odd for November in Connecticut -- but it’s sunny, and Rory’s deciding to take that as a good sign, a sign that everything is fine, because as they drive all she can think about is everything that could be wrong. The baby’s dead already. It has two heads. It’s twins, oh, god, it’s twins, isn’t it--

“You’ve been unusually quiet,” Lorelai observes after she parks the car. “What’s on your mind?”

Rory taps her fingers on the door anxiously. “Nothing,” she says. “Just...thinking.”

They wait for about twenty minutes in the waiting room until a nurse comes out and says Rory’s name. The nurse leads them to an exam room and tells Rory, “The doctor will be in in a few minutes.” She leaves the paper dress on the seat. Then she leaves and the door clicks shut behind her.

Rory changes and sits. Lorelai stands at her side, taking Rory’s hand in hers. “You got this, kid,” she says soothingly, and for a moment, all of Rory’s worries are gone.

But then door opens and a middle aged woman in a lab coat walks in, and all the fears are back. “You must be Rory,” she says. “I’m Doctor Kim.” Her voice is deep and kind, nice to listen to. “How are you, dear?”

“Good,” Rory mumbles, suddenly feeling very shy. She’s always been this way with doctors -- no clue why. 

“And you are?” She asks Lorelai. 

“Her mom.”

“Oh, good, good,” Dr. Kim says. “Alright, Rory, let’s get started. I’m just gonna do a checkup first.”

She takes Rory’s blood pressure, weight, height, heartbeat, and checks her mouth and her ears. There’s exams, checking to make sure there’s nothing wrong, and then Dr. Kim draws some blood, and Rory is scared she’ll faint (she doesn’t), and Dr. Kim asks for a urine sample.

Once everything is done, the tests come back fairly quick. “No STI’s, no anemia, no diabetes, no infections. You’re in perfect health, Rory,” Dr. Kim reports cheerfully. “Which makes it easy for us to move on to the next part of your visit. I’m just going to ask some questions, okay?”

Rory nods. “Okay.”

“Any history of chronic health problems in your family?”

“Uh, my grandpa died of a heart attack,” Rory replies nervously. “Does that mean I’m at risk?”

“Not necessarily,” Dr. Kim replies. “It’s just important that we get all the information we can.”

Rory nods, but she doesn’t feel any more comforted.

“Any history of smoking or drugs?”

“No.”

Dr. Kim continues to ask questions. When she is finished, she turns on the machine next to Rory. “We’re going to do the ultrasound now,” she says.

“This is the fun part,” Lorelai murmurs. 

The gel is cold, and Rory almost laughs when it’s applied, but she manages to sit still. Dr. Kim places the wand, and sure enough, the image is on the screen.

Rory watches in awe. She knew she was pregnant, sure, but this -- oh, this is so different, but in a good way. 

“You see that?” Dr. Kim asks, pointing to a small little spot on the screen. “That’s your baby.” Lorelai squeezes Rory’s hand. Dr. Kim keeps talking, but Rory doesn’t register any of it. 

“And everything’s healthy?” Rory breathes.

Dr. Kim smiles. “Everything is healthy.”

Looking at the ultrasound, for the first time in a while, Rory can breathe again. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory can’t stop smiling on the way home. She holds the printout in her hands, looking down at it, holding it up, trying to commit every detail to memory. 

Lorelai grins when she sees this. “Pretty cool how that's inside you, right?”

“Yeah,” Rory murmurs. “Yeah, it is.” 

She was scared before, yes, and she still is -- but now, along with that fear, there’s hope. A hope that she’s not planning on letting go of any time soon. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

After his talk with Rory the other day, Jess notices how much more comfortable he feels around her. There are finally no secrets between them -- besides for the fact that he still loves her, but that’s neither here nor there, he decides -- and that lack of secrets finally eases the tension. He’s glad she knows about his dating life. He’s glad that she told him about Logan and Paul. That’s what friends tell each other. It’s one step further from being just-exes to being exes-but-best-friends. And Jess hopes that someday, he’ll be able to reminisce about the days when they were still together. That someday, he won’t be so hung up on his mistakes and failures. That’s the destination, he thinks. That’s the goal. And he thinks that they’re close to being there, he really does. 

Rory is out for the day, and Luke doesn’t need help in the diner, so Jess goes to the bookstore. He’s finished all the books he brought, and Andrew has a tendency to stock obscure books right alongside the classics, so he’s itching to see what’s available.

Jess leaves with three new books -- he figures that even if he zips through them, they’ll last about a week if he keeps hanging out with Rory and helping out at the diner. But, he can’t help but open one and read as he walks. So maybe make that four days.

Jess is so engrossed in the novel that he barely gets anywhere before running into someone. Startled, he drops his bag and books, and whoever he ran into yells, “What the hell?” The voice is very familiar, he realizes.

“Sorry,” he apologizes, gathering up his belongings and the cell phone that the other person dropped. He straightens up, only to find himself face to face with Shane.

Jess freezes. Shane’s pissed off expression has transformed into one of confusion.  _ “Jess?” _ She exclaims.

Jess hands her back her phone. “In the flesh.”

“What are you  _ doing _ here?” She questions him. 

“I’ve been here for three weeks,” Jess deadpans.

Shane blinks a couple of times before replying. “Oh,” she merely says. 

Jess stands there, awkwardly, trying to see if she’s expecting him to keep talking or to leave. “How are you?” He asks.

“Fine,” she snaps -- not angry, it’s just the way she speaks. It’s quiet again, and Jess considers just saying goodbye and walking away, but she speaks again. “I’m married,” Shane informs him out of the blue. 

It’s Jess’ turn to blink in surprise. “Huh,” he says when she shows him the ring. 

“Three years next month.”

“Congratulations.”

“...What about you?” She asks uncomfortably. 

“Nothin’ going on.”

Shane raises her eyebrows. “You’re not still with Rory?” 

“What?” 

“Well, obviously not  _ still  _ with her, but I meant...you’re not together?” 

“No,” Jess replies, puzzled. “We’re not.”

“Oh.” She shoulders her bag and turns to leave. “Could’ve fooled me,” she says, and then walks off.

Jess stands there, stunned. Not only did running into Shane throw him off by itself, but that brief conversation sent him spinning. Why did she think he was dating Rory? Where in hell did she get  _ that _ idea from? Is he really that obvious? Has Rory caught on to how he feels?

But Jess shakes it off and continues his walk back to the diner. He promises himself that it’s no big deal. Shane was never the most observant, he thinks, trying to soothe himself -- but in reality, he never really knew her all that well. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory calls up Emily the night after her appointment. Emily deserves to know, and nothing, not even her grandmother's disapproval, can bring Rory down right now. 

“Rory, dear, how are you?” Emily asks as soon as she picks up. “And how’s your mother? Is she home from her honeymoon yet? She said she’d call, but she never did…”

“I’m good, Grandma,” Rory replies, trying not to laugh. “And mom’s good. She’s just been busy.”

Emily scoffs. “Doubtful. What’s she been doing?”

“I actually called because I have something to tell you,” Rory says, ignoring Emily’s question. “It might be...surprising, but…”

“What is it?” Emily inquires, sounding concerned. “Is everything alright?”

Rory closes her eyes and takes a deep breath. “I’m pregnant.” The other line is quiet. “And I know it’s not in the way that what you want, but--“

“Rory,” Emily interrupts firmly, “I’m happy for you.”

Rory blinks, dumbfounded. “You are?”

“Yes,” Emily confirms. “Oh, I just wish your grandfather could be here for this…”

“Yeah, me too,” Rory says softly. 

Emily sighs. “More and more women are having children when they’re not married, so I suppose it’s kind of silly to be upset about that. I just hope you’re happy with this,” she says tentatively, as if unsure if it’s the right thing to say.

Rory smiles. “I am.” She tells her grandmother about the appointment and the ultrasound, and Emily’s replies are full of excitement, which only makes Rory happier. 

When the call is over, Rory can hardly believe what just happened. She’d prepared herself for her grandmother to be upset, scold her, insist to be a part of everything, pressure Rory into telling her who the father is and what his role will be...but looking back, it feels almost foolish. But it’s apparent that Emily learned from the first time what not to do. It took her awhile to get there, but she’s here  _ now _ , and that’s what matters. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

She only just made this drive two months ago, but it’s unfamiliar the whole way up.

Rory stares straight ahead of her, trying to ease her nerves. The road is empty except for her, and the once scenic drive full of autumn leaves is now cold and bare. But she has a mission, something to accomplish, and this dreary day isn’t going to stand in her way.

She’s driving up to her father’s office, as if the last meeting was such a success -- but he deserves to know that he’s going to be a grandfather. Even if Rory is still reeling from their last meeting, she has to tell him. He has to hear it from her.

Christopher is surprised to see her, but happy nonetheless -- “I didn’t know you were coming,” he says, but he’s smiling just a little.

“Yeah, it was a little impromptu,” Rory explains. She feels a little awkward. He seems to as well. 

Christopher clears his throat and steps aside. “Come on in.”

Rory takes a seat in the chair, and he sits behind his desk. “What’s up, kiddo?” 

Rory taps her leg anxiously. How does she go about this? How does she tell him this bombshell of a secret? A man who’s rarely ever there?

“Something wrong?” He asks, concerned.

She shakes her head. “No, no, I…” She swallows. Her heart is suddenly beating a million miles a minute. “I have something to tell you.”

“Shoot.”

“I’m pregnant.”

His eyes widen, blinks a few times, opens his mouth but then closes it--

“I just thought you should know.”

“Well, that sure is something, kiddo,” Christopher finally says, and all Rory can think about is Logan -- is this her future? A childhood full of barriers and miscommunications? Is this all she has to look forward to? “Congratulations.”

It all feels very artificial, and as much as Rory  _ wants  _ to blame him for it, she can’t. This relationship has been dry for ages -- a father and a daughter who feel like even less. Because he was never really there, and even if he’s tried and he’s talking to her now, it isn’t enough. It just didn’t work. And that isn’t his fault, as much as she wants it to be. She can’t bring herself to hate him. “Thanks, dad.”

He doesn’t know what to say, Rory can tell. He doesn’t know what to say to this. Par for the course. 

Christopher folds his hands in front of him. “I do have work to do, so…”

“Right. I’ll go.” Rory stands up and smooths her dress out. “Well...it was nice to see you.” It’s a lie, and she knows it, and he does too -- but he still nods and smiles and says it was nice to see her too. 

Once out of the office, Rory presses her back up against the door and closes her eyes. She takes a deep breath.  _ It went as well as you thought it would, _ she reminds herself.  _ No reason to feel disappointed. _ But even as she says that,  _ disappointed _ is all she feels. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

It’s Friday night in the Gilmore House, which means it’s movie night. Rory orders takeout and sends Jess to get it -- with the promise of a tip. Lorelai and Rory sit on the couch trying to pick out a movie, while Luke hooks up a VCR player.

“I don’t know why you won’t go digital,” Luke grunts from behind the television. 

“Why would we do that when we have you to do all the labor for free?” Lorelai asks innocently. 

“And what would we do with all our tapes?” Rory adds. 

Luke sticks his head out from behind the television. “Throw them out.”

Lorelai gasps. “How dare you! I’m keeping them forever.”

“The minute I finish this, I’m filing for divorce.”

Lorelai opens her mouth to retort, but the doorbell rings. Rory stands up to get it -- when she opens the door, Jess is there with the takeout. “Tip?” He asks when she takes it from him.

“I’ll think about it,” She replies over her shoulder, bringing the takeout to the coffee table.

“Ooh, Chinese!” Lorelai cheers. 

“Save some for Luke,” Rory scolds her mother as Lorelai grabs two boxes. 

Jess takes a seat next to Rory on the end of the couch. “You ordered enough for a circus troupe,” he observes. Lorelai shakes her head, mouth full of food.

“You haven’t eaten with us in a while, so you might’ve forgotten how much we can eat,” She tells him. 

“It’s possible,” He agrees. “Mind sharing?”

“Oh, please, go ahead,” Lorelai says. “I’m going to get some plates,” She announces, and heads to the kitchen. 

“Guess who I ran into the other day,” Jess says suddenly, crossing one leg over the other. 

Rory pauses. “Taylor?” She guesses.

Jess shakes his head. “Nope.”

“Kirk?”

“No.”

“Lane?”

“Nope. How is she, by the way?”

“Fine, I give,” Rory says. “Who?”

“Shane,” Jess informs her, and Rory’s eyes widen.

“Seriously?”

He nods. “Yep. Ran into her quite literally when I was leaving the bookstore.”

Rory shifts uncomfortably. “How is she?”

“Dunno,” Jess shrugs. “Wasn’t a very long conversation.”

“What did she say?”

Jess leans forward and grabs one of the boxes. “She’s married.”

“Wow.” Rory blinks a couple times. “Shane. Married.”

“How do you not know this?” Jess questions her, opening some chopsticks. “You live in the same town.”

“I don’t really live here,” Rory says. “Just...staying here for the time being.”

Jess shrugs. 

“Who’s she married to?”

“She didn’t say,” Jess replies, “but for three years, apparently.”

“Wow,” Rory repeats. She goes quiet. 

Jess elbows her. “Hey, I know what you can give me as a tip.”

“Hm?” She hums, leaning forward taking some kung pao chicken.

“You still owe me an egg roll,” he reminds her, a playful smile on his face. 

Rory laughs. “Oh, God, right. I forgot about that.”

“Forgot about what?” Lorelai asks, returning with a stack of paper plates.

“That’s bad for the environment,” Jess points out.

“I don’t want to do the dishes.”

“How much have you forgotten since you’ve eaten with us?” Rory asks Jess in astonishment. 

A large thunder clap sounds, and Lorelai jumps, dropping all the plates. “Aren’t you glad those were paper?” She asks, bending over and picking them all up. 

“I owe him an egg roll,” Rory explains, answering Lorelai’s previous question.

Lorelai takes a seat again on the other side of Rory. “I got that much.”

“About fourteen years overdue,” Jess comments. 

Rory gives him a look. “You never collected on it.”

“Someone fill me in?” Lorelai interjects.

“It was a bribe,” Rory remembers. “Back when I was Stars Hollow’s censorship queen?”

Lorelai snorts. “Oh, my god. The curtain incident.”

“What was I bribing you for?” Rory asks Jess.

“I think I taped over some of the children’s movies with certain adult content,” he recalls. 

“Was I asking what movies?”

“I don’t think so,” Jess says. “I think you were just trying to find out what I did.”

Rory nods. “Sounds about right.”

Lorelai snorts. “God, I feel bad for the kids who picked up those movies.”

“Nothing a little  _ Eyes Wide Shut _ can’t fix,” Jess muses.

“Jess!” Rory exclaims. 

He shrugs. Lorelai shakes her head. “Disappointing. I was expecting something more... _ Unfaithful,” _ she concludes. “Try harder next time.”

“That’ll take another egg roll,” Jess says. Rory hands him two. “Please doing business with you,” she says, grinning.

Rory smiles softly, and the moment is back -- one they’ve had so many times before -- but then Luke announces he’s done hooking up the VCR, and it’s over again.

Throughout the movie, Jess is extremely aware of Rory’s arm continuously brushing up against him, when she laughs so hard she leans into him, or when their hands brush when she hands him more egg rolls. But he pretends not to notice. And he also pretends not to notice Lorelai’s knowing looks -- Luke probably told her about what he’d revealed, especially since she’d had the suspicion in the first place…

But, he ignores it. Because for the first time in thirteen years, he’s once again attending movie night at the Gilmore’s. It feels a little strange that they’re welcoming him back with open arms, and it digs up bittersweet memories, but it mends a hole that he didn’t know was there. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

When the movie is over, it’s still storming. Jess looks out the window apprehensively -- he walked over, and isn’t looking forward to braving the heavy rain. “Hey, Jess, come get a fortune cookie!” Rory calls from the couch. 

He sits down and takes one, cracking it open. “What fortune did you get?” Lorelai asks Rory. 

“‘A good time to finish up old tasks,’” Rory reads. 

“Oh, we’ve gotten that one before.”

“What’s going on?” Jess asks, puzzled.

“Al has sixty-four different fortunes,” Rory explains. “We’ve been trying to collect them all for, like, twenty years.”

“‘An inch of time is an inch of gold,’” Lorelai reads. “Nah, we already have this. Trash it.”

Luke cracks opens his cookie. “‘Believe it can be done.’”

“None of these are actually fortunes,” Jess points out. 

Lorelai merely shrugs. “Read yours,” she instructs.

“Fine, but I think it’s pointless,” Jess sighs. “‘A good friendship is always more important than a good romance.’”  _ Fitting,  _ he thinks to himself. 

“We don’t have that one, do we?” Rory asks her mother excitedly. 

Lorelai shakes her head. “Add it to the collection,” she says. Rory grabs a tin and opens it. Sure enough, there are tens of fortunes inside -- Jess hands her his, and it is added to the collection.

“Is it still storming?” Luke asks, punctuated by a loud  _ boom. _

“I’d say so,” Jess says. “I better get going in case it gets worse.”

Lorelai frowns. “Hey, Jess.” 

“Hm?” He asks, standing up and stretching. 

“Why don’t you crash here tonight?” Lorelai offers. “It doesn’t seem like it’s going to be letting up anytime soon.”

Jess shakes his head. “It’s fine. I can brave it.”

“It’s pouring rain and it’s 40 degrees,” Rory objects. “You’ll get sick.”

“Really, I’ll be fine.”

“Just sleep here,” Lorelai insists. “No harm, no foul.”

“Never thought she’d be begging him to stay,” Luke says to Rory, who snorts in agreement. 

Jess hesitates. As unappealing as walking in pouring rain is, especially without a rain jacket or umbrella, he feels a little uncomfortable staying overnight. Back when he got here for the wedding, Luke had offered to let him stay with them, but Jess had turned it down. It’s difficult to put into words, but staying overnight at his ex’s? He’s fine without it.

But on the other hand, it’s storming, it’s late, and it’s cold. “Okay,” he surrenders. “Thank you.”

Rory frowns. “It’s rude to make him sleep on the couch,” she points out. 

“I’m fine with it, really,” Jess assures her, but Rory doesn’t seem convinced.

“Take my room,” she insists. “I can sleep on the couch.”

“I’m very good at crashing on couches. It’s like second nature.”

“Learn to adapt, Darwin.”

“Enough arguing,” Lorelai interrupts. “I’m this close to making the both of you sleep on the couch.”

“I’m working on my book tonight, anyway,” Rory says, “So I won’t be sleeping much.”

“Your desk is in your room,” Jess points out.

“I can write on the couch.”

Jess shakes his head. “You played all your egg rolls too soon.”

“I can show you my withering stare,” Rory offers.

“What?” Luke and Lorelai say in unison.

Jess hesitates. For whatever reason, Rory  _ really _ wants him to crash in her room -- or, rather, she doesn’t want him sleeping on the couch. “Fine,” he concedes. “Jeez, the lot of you…”

Rory shoots him a smug look. “Good.”

The conversation tapers off, and Jess sits down awkwardly, all too aware he just agreed to take his ex-girlfriend’s bed while she takes the couch, and how weird it is. And while as a teen he’d imagined sleeping in her bed, the circumstances were way different. And now? It just doesn’t feel right. But Rory cares about him, and doesn’t want him to be stuck on the couch while he’s already stuck in the house, so he’ll take it. Plus, he’d be lying if he said it didn’t make his heart glow just a little bit more. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory sits at the kitchen table, laptop open, but she struggles to focus. Jess agreed to crash in her room, albeit reluctantly -- she wanted him to be comfortable, as he is a guest. He left the door open, and she’s unsure why, and how he managed to fall asleep with it open, she’ll never know -- but he’s been dead asleep for hours. He snores, too, a fact that Rory finds incredibly endearing. She keeps looking over at him, and she  _ knows  _ it’s creepy, and she should just go over there and close the door, but it’s hard to stop. He looks so peaceful, she thinks to herself. It’s nice to see. 

While the image of him in her bed always had a different context when they were together, she’d definitely considered it before. And she shouldn’t be considering it now, she knows -- the last thing she should be doing is staring at him like this. The last thing she should be doing is thinking about him like this. Because she can excuse dreams, but this -- she’s just tired. Or maybe it’s still the hormones. There’s a million things it  _ could  _ be, and there’s one thing it certainly isn’t. For the thousandth time, she reminds herself that she doesn’t have feelings for him -- something she’s had to tell herself a lot lately. 

She forces herself to tear her eyes away from him, and fix them on her laptop. Excitement and apprehension flow through her as she begins to type. 

_ Chapter Eight: The Road Trip to Harvard.  _

**Notes for the Chapter:**

> if milo doesn’t win his emmy on sunday we riot thx


	9. Wouldn’t It Be Nice?

**Summary for the Chapter:**

> Paris gives Rory advice that sends her spiraling. Jess disappoints his friends.

**Notes for the Chapter:**

> i’m sorry this took a while — school’s been kicking my ass lately. i know this is a filler, but it’s only because the next chapter is not, and i didn’t have really anything for this one. im also trying to put less pressure on myself to make the chapters long, so they might be a little shorter now, but it really depends. thank you guys for being understanding!! hope u enjoy!! next chapter is gonna shake things up.

Three things run through Jess’ mind when he wakes up the next morning. One: he should’ve closed the blinds. Two: He’s still in a t-shirt and jeans. Three: This isn’t his bed.

He pushes himself up into a sitting position, still adjusting to the bright light streaming through the window. He fell asleep almost immediately the night before -- he’d been so tired and anxious that he’d even forgotten to close the door. It’s closed now, he realizes as he kicks off the covers and gets out of the bed. 

He’s a little alarmed at how reluctant he is to get out of bed -- the previous night, he had been so anxious to get the whole night over with. And now? He just wants to lie there and breathe in Rory’s scent all day.

Jess shakes it off and opens the door, stepping into the kitchen. He smiles to himself when he sees Rory. She’s dead asleep, laptop in front of her, head resting against the table. He doesn’t want to wake her up -- he has no clue how long she was up or how long she’s been asleep. So, instead, he grabs a blanket from her bedroom and drapes it around her shoulders before grabbing his things and leaving the house. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory wakes up with a sore neck and a blanket around her shoulders, both of which she definitely had not fallen asleep with. She blinks a couple times as she sits up, stretching her neck despite the soreness. Her bedroom door is open, she notices -- and Jess is gone. She smiles to herself as she realizes this blanket is one from her room, and Jess most definitely put it on her as she slept. He’s such a good guy, she thinks to herself, a warm feeling in her heart.

Rory is almost, almost,  _ almost  _ ready to tell Logan -- she’s been working herself up to it, telling others, but it’s still a challenge, a huge hurdle she has to jump to get to it. But she’s trying, and that’s what counts.

Jess still doesn’t know, and Rory knows that once he does, it’s going to change everything. Her fear that he’ll leave is fading, but it’s still there -- she knows he’s grown up, and he’s mature, and kind, but every other time he hasn’t been is still burning in her mind. And this time, they’re not in a relationship, and he has no obligation to stay, not at all. So she really can’t blame him if he skips town when he finds out.

She’s getting closer to writing about Jess in her book, too -- she’s not quite down with her Harvard chapter, discussing her dreams of going there paralleling with her and her mother’s road trip there back in junior year. When she does, she knows that she writes about him next. And she’s a little worried, scared, afraid of what realizations she’ll uncover when she does. Whenever she writes about Dean now, she’s hit in the face with the bad memories, the ones she buried so deep down she’d nearly forgotten. Will there be more? Will it be the same with Jess?

_ I can write later, _ she thinks to herself, standing up and making herself a pop tart and some coffee.  _ I’ll get to it later. _

Her open laptop seems to judge her. 

“I just don’t want to write about him right now,” she says aloud.

The computer is silent.

“Don’t give me that look.”

“What look?” Lorelai asks sleepily, coming down the stairs in her work clothes. 

Rory shakes her head. “Nothing.”

“Hey, can you give me some coffee?” She asks, collapsing into the chair Rory was sitting in. “I feel like I have a takeout hangover.”

Rory frowns, grabbing another mug. “What’s a takeout hangover?” 

“I don’t know, but I have one,” Lorelai replies, massaging her temples.

“I’ll call Doctor Oz,” Rory quips. “He’ll he floored by this new discovery.”

Lorelai dismisses Rory’s comment with the wave of her hand. “You didn’t have to sleep at the table,” She points out, holding up the blanket. “You could’ve taken the couch.”

“I didn’t fall asleep on purpose,” Rory defends herself. “Sometimes it happens when you try to stay up all night writing a book.”

“My little author,” Lorelai croons. “Your neck is going to snap one of these days.”

“I didn’t even bring the blanket out,” Rory adds defensively. 

Lorelai’s brow furrows. “What? Did it grow legs and walk out here?”

Rory flushes pink. “Nevermind.”

“No, no, I’m intrigued now,” Lorelai says, suddenly alert. “I need to hear the answer to the great blanket caper of 2016.”

“Fine,” Rory concedes. “I  _ think, _ and I don’t know for sure -- I  _ think _ that Jess wrapped it around me before he left,” she admits, gesturing to her open bedroom door.

Lorelai clutches her heart. “He’s a good kid after all, huh?”

“He always was,” Rory argues. “Deep down.”

Lorelai merely shrugs. Then, a devious smile spreads across her face. “You and Jess seem to be getting really close, then.”

“Yeah.”

“ _ Close,” _ Lorelai emphasizes.

Rory grabs her pop tart from the toaster. “Mhm.”

“Closer than before.”

“What’s your point, Detective?”

“Is this whole ‘I don’t have feelings for Jess’ act going to go away anytime soon?” Lorelai asks wearily. “I have other things to do.”

“It’s not an act,” Rory argues.

Lorelai raises an eyebrow. “Are you sure? Because, I don’t know...this is all feeling very 2002.”

Rory hands Lorelai a mug of coffee. “Jess and I are friends. We’re both long over this.”

“So, you don’t love him?”

“You want this coffee in your face instead?”

“Rory.”

Rory rolls her eyes. “Like I said, I’m past this. I’ve moved on -- twelve years ago, in fact.”

Lorelai presses her lips together, but doesn’t say anything. 

“Mom.”

“Mm?” Lorelai replies, going over to get herself a pop tart. 

“You believe me, right?”

Lorelai turns around to face Rory, who stands on the other side of the table. “I just want to make sure that you believe yourself.”

Rory sighs. She locks eyes with her mother and says, firmly, “I don’t love Jess.”

“Okay. I believe you,” She promises, and that’s the end of that. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Paris is in Stars Hollow for a day to visit, merely passing through, she promises. Rory insists on taking her to lunch, and Paris agrees (albeit reluctantly, she’d much rather discuss literature and the pregnancy over some coffee in Rory’s house), so they arrive at Luke’s around noon.

Rory is pleased to see Jess behind the counter, while Paris is simply confused. “What are you doing here?” She asks without hesitation, marching up to the counter. No time for niceties.

Jess looks up, his look immediately turning into one of amusement. “Long time no see,” he muses. “What’s it been? Fourteen years?”

“Just about,” Paris snaps. “But you didn’t answer my question.”

“He’s just staying in town for a little while,” Rory explains. “Sit down, come on.”

Paris takes a seat on a stool next to Rory, still watching Jess carefully, as if she’s worried he’ll make a sudden, unpredictable movement. 

After they order, Jess returns, wiping down the counter. He focuses on a specific spot and scrubs it roughly. Rory takes a sip from her coffee, listening to Paris talk about her clinic, although most of the words are going right over her head. 

“...monthly report, but I don’t think they’re going to get anywhere close to our success,” Paris finishes, seemingly unaware of Rory’s inability to focus on this topic. Rory looks over to Jess for help. She doesn’t want to hear about the monthly report. 

“Paris,” he says, leaning forward, “any interesting reads lately? I’m interested to hear your take.” His eyes sparkle playfully, and Rory knows he’s expecting an argument to start. She tries to send him a mental  _ thank you. _

“Haven’t had much time to start anything, considering I run a very successful surrogacy clinic,” she snaps. Jess raises his eyebrows. 

“Impressive.”

“Have you heard that they’re making a television show out of the Handmaid’s Tale?” Rory suggests, because this isn’t going anywhere. 

Paris rolls her eyes. “God, as if we need to lose more readers to the brainless masses whose only purpose in life is waiting a week for the next episode of the latest incoherent adaption of great literature, the world will be  _ screwed.” _

Rory laughs. “Maybe, maybe not.”

“I don’t believe in movie or TV adaptions,” Jess says. “They never do it justice.”

“And yet, you see every single one,” Rory points out.

Jess laughs. “Still interesting to compare it to the book.”

Paris scoffs. “Please. I doubt you’ve read  _ the Handmaid’s Tale,  _ or anything even close to it.”

“Hey, I have, too,” Jess says defensively. “I loved it.”

“Really.”

“Really,” he says. 

Paris nods. “Alright, then.” Pause. “It really  _ has  _ been a long time, huh?”

“Been a few millennia.”

Paris reaches into her purse and hands Jess a business card. 

“Uh, you know, I’m not really looking to have a kid,” Jess says skeptically, taking it from her. 

“It’s to stay in touch,” Paris snaps. “God,  _ men _ .”

Jess frowns in confusion.

“I’d be interested to hear your takes on other novels,” Paris explains. “Feel free to call about whatever you’ve read lately.”

Jess nods. “Solid.”

The three of them continue talking, laughing, but there’s a twinge in Rory’s heart the entire time. It really  _ does  _ feel like the old days, and she misses them. She misses them a lot. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

After stopping at the diner for lunch, Rory and Paris walk around town in the chilly November air. “I’ve already got a chunk of the first draft done,” Rory tells her excitedly. “It’s going really well.”

“Have you considered publishers yet?” Paris asks.

“I’m not done with it, so, no.”

Paris rolls her eyes. “Come on, Rory. You’re going to have a child in -- how many weeks are you?”

“Eight,” Rory says slowly. 

“In seven months,” Paris continues. “You need to get a publisher  _ now, _ someone who likes what you have so far, before you’re too busy to find one.”

Rory blinks a couple times. “Are you sure? I can’t wait?”

“I mean, it’s your career whose grave you’re digging if you don’t,” Paris shrugs. “But if you want to be prepared, you’ll do it now.”

Rory frowns. She hadn’t thought about this at all, but now that she is, she probably should have ages ago. Paris is right -- once she has her baby, she’ll be too busy, too busy for a while, especially if she’s doing this on her own. 

Paris offers to send her different publishers’ info and interview tips, and Rory accepts, still preoccupied by her thoughts. Has she not been taking this seriously enough? Has she not been thinking it out enough? She feels like she did when she was applying for college, realizing that she needed more extracurriculars or that her essay was too basic for any prestigious university. She’s been feeling so lost lately, and this only goes to show how lost she truly is. She wants to talk to her mom, she wants to get this taken care of, but most of all, she wants to talk to Jess. But she knows she can’t, because he doesn’t know about the baby, and that’s what stings. She wants to tell him, because for a lack of a better word he’s her best friend, and she wants to tell him everything, even if she knows she can’t. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Luke and Lorelai probably have better things to do than discuss Jess and Rory, but, hey, the diner is closed for the night and nothing is on TV. “Rory says she doesn’t love him,” Lorelai says, kicking her shoes off. 

“Do you believe her?” Luke asks.

Lorelai nods. “I do. I don’t think she’d lie about this, not now.”

“Jess still loves her,” Luke sighs. “I hate to see him like this.”

“It’s a doozy,” Lorelai agrees, sitting up against the headboard. 

Luke shakes his head. “He can’t find out she’s pregnant,” he says. “It’ll shatter him.”

“He’s going to find out eventually,” Lorelai points out. “I just hope she hears it from him.”

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess has been in Stars Hollow for about three weeks now, so he figures he owes Chris and Matthew another call. He’s been in touch with them, texting mostly, but a phone call is the least he can do when he really has no idea when he’s coming back. They answer fairly quickly. 

“How’s it going over there?” Chris asks when Jess says hello. “Got the girl yet?”

“I’m hanging up.”

“Wait, wait, man,” Chris laughs, “Hold up. Matthew, get over here. It’s Jess.”

Jess hears a  _ click,  _ so he knows he’s on speaker. “When are you coming back?” Matthew demands immediately. “I don’t like you spending so much time over there with that girl.”

“And we’ve been having to do a  _ lot _ of extra work because you decided to play best friends with your ex,” Chris adds. 

“We haven’t had  _ that _ much wo-- ouch!” Matthew exclaims, and Jess figures Chris elbowed him. His friends are worried about him, which he appreciates a lot, even though they don’t have to be. 

“Thanks, mom,” Jess replies, rolling his eyes. “But it’s all good on the home front here. My uncle wants me to stay for the holidays, and I haven’t given him an answer yet, but…”

Matthew groans. “Come on, man, this is pathetic.”

“It’s not just about her,” Jess argues. “I don’t get to see my uncle much, you know. It’s nice to spend time with him.”

“And it has nothing to do with she-who-must-not-be-named?”

Jess sighs. “Look, I get that you’re worried about me, I do, but you don’t have to be, okay? It’s all good.”

“She’s got some unworldly hold on you, dude,” Chris says. “You need to get out of there.”

“Remember: Rory  _ bad,  _ okay?” Matthew adds. “This is the same girl who broke your heart into a million pieces, Jess.”

Jess snorts. “You still haven’t forgiven her?”

“No, and you shouldn’t either,” Matthew states. “She fucked you up real good. That doesn’t just go away overnight. You should hate her. Like me.”

“She’s a good person,” Jess retorts. “She’s just had some ups and downs. Just like anyone else.”

“Yeah, but they were at your expense,” Matthew points outs 

Chris sighs. “Matthew may be being a little harsh--“ 

“You  _ think?” _ Jess exclaims. 

“But he’s just concerned, okay? So am I. This has gone on long enough. Come home, Jess.”

Jess closes his eyes and swallows. There was been a time where he would have jumped to leave Stars Hollow at the first chance he got, a time where he would’ve crumbled upon hearing someone tell him to  _ come home.  _ But even if it warms his heart to hear his friends  _ care,  _ which had been a foreign concept for so long, he’s just not ready to leave. “I can work from here for now,” he says. “I just...I’ll stay through the holidays. Rory’s one of my best friends now, guys. And I...who knows what will happen?” He bites his lip, cringing at the hope in his voice. 

“See, man, you’re getting your hopes up!” Matthew exclaims. “What’s she doing to you?”

“No, not like that,” Jess says quickly. “I mean...I don’t know what I mean.”

Matthew begins to speak, but Chris cuts him off. “You’re still  _ this  _ crazy about her, Jess?” His voice is softer, less harsh, and Jess softens.

“I just want to be wherever she is,” he says weakly. 

Chris sighs. “Alright, man. We’ll send some work your way. We’ve got a bunch of new applicants for clients, and you’re always the best at weeding through them.”

“Will do,” Jess says, clearing his throat. “Thank you.”

“Just don’t get hurt again, okay?” Chris says.

“No confessing to her,” Matthew adds sternly.

Jess laughs. “Okay. I promise.”

He says goodbye and hangs up, taking a deep breath and exhaling slowly. He loves his friends, he really does, no matter how crazy they are. He owes them at  _ least _ one souvenir each, he thinks to himself.

**Notes for the Chapter:**

> love u guys 😌


	10. Career Opportunities

**Summary for the Chapter:**

> Rory takes out her frustrations on Jess, but it's her secret that sends them both reeling.

**Notes for the Chapter:**

> ah, yes, the infamous chapter ten is finally here. buckle up folks cause shit gets real from here on out  
also please forgive me and suspend your disbelief here i don't know how these interviews work

Rory took Paris’ advice. Of course she did, she always does -- but she’s wishing now that she’d just left well enough alone. Because now, she’s sending her proposal to just about every publisher she can find on Google, and she gets the same answer every time.

_ Your book needs to be finished, _ everyone says. _ Stay in touch and resubmit when it is. _

She should’ve waited. Because even if she has a chance when she’s done, when will that be? She’s going to have a kid. And before that, preparing will take up a lot of her time, too. She needs to get done what she can _ now. _

She can’t help but feel humiliated, though -- humiliated that she got shot down so many times for something so simple. She wants to do things right the first time, a habit she’s always had. And now, what if this tarnishes her record? What if she’s screwed herself over? She’s spiraling, she knows she is, but she can’t help it. It’s so hard to tear herself away from the idea she’d formed in her head so quickly. 

Rory is about to close her laptop and search the fridge for some leftovers when she gets a notification. An email from HarperCollins. 

_ Dear Ms. Gilmore, _

_ Thank you for your interest in publishing your memoir with HarperCollins. We enjoyed your book proposal and are interested in going through with publishing. First, however, an interview is required. Email back with some times you are available and we will get back to you as soon as possible. Prepare a portfolio… _

There’s more, but Rory is sure her brain has short-circuited. She reads the email multiple times, unsure if she’s reading it correctly. An interview? She can hardly believe it. Rory emails back right away, a grin on her face, because finally, finally, finally -- she just might be falling back together. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Despite turning down Chris and Matthew and refusing to go home, Jess wonders whether or not they’re right. Because as defensive as he can be, they have a point -- being around Rory for the long term is only going to hurt him more. His friends may be a little harsh, but their hearts are in the right place. They’ve seen first hand how much she’s hurt him before. They don’t want him to feel like that again. He isn’t too keen on it, either. 

So, the next morning, Jess makes a decision. He’s been here long enough. Luke doesn’t need any help at the diner, and he’s not really doing any good here, so he decides to leave the next day. He’ll let Rory know when she gets back home -- she’s going out to the city today, according to Lorelai -- and then he’ll pack his bags and go back to Philly.

Jess misses his friends. He misses his job. And although none of that compares to the way he misses Rory when he’s in Philadelphia, that’s the kind of longing he’s learned to deal with. He needs to rip off the bandaid and just _ go. _

It’s for the best, he promises himself. This will be the best for everyone. He believes that, he truly does, but as much as he wants to _ want _ that -- which is so, so much -- he just can’t. Wanting to leave her has never been something he’s craved. But he finds himself doing it every time. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory wakes up the morning of the interview invigorated and refreshed. After what felt like years of a rut, she’s been working her way back for months, and now, here she is, on her way to interview for HarperCollins.

She ditches her lucky red dress for a nice blue one, figuring it didn’t bring her much luck anyway. She also decides to leave her hair down and wear some nice flats. She doesn’t want to seem like she’s trying too hard. That’s never the right way to go. 

It’s a few hours drive up to the headquarters in New York, but it seems to go by quickly -- maybe it’s the excitement coursing through her, or maybe it’s the coffee. Either way, the drive is over in the blink of an eye, and suddenly, she’s standing in the lobby. 

The secretary tells her where to go, and soon, she’s shaking hands with a woman named Pauline. “It’s nice to meet you, Rory,” she says sweetly. “Here, have a seat.”

Rory takes a seat on the sofa, while Pauline sits in a chair facing her, holding Rory’s portfolio. “So, Rory,” she begins, “Let’s start with your work experience. What kind of jobs have you had?”

“Oh, uh…” Suddenly, Rory wishes she had prepared more. She had been so excited that she had scheduled the interview as soon as possible, which was only a couple days after receiving the email, and hadn’t done much to prepare. “Well, I worked for my high school newspaper...although, mind you, the first year, I mostly did articles on repaving the parking lot and other stuff like that because the editor _ hated _me. We’re good friends now, though.”

Pauline raises an eyebrow at Rory’s nervous rambling.

“Of course, that wasn’t the only job I’ve had,” Rory adds quickly. “I was editor of the Yale Daily News in college. I also interned at the Stamford Eagle Gazette. After I graduated, I reported on the Obama campaign, and currently I run the newspaper in my hometown, and…did you see my New Yorker piece?” She ends weakly. She can hear Jess’ voice in her head, saying, _ get it together, Gilmore. _

_ I’m trying, _ she tells the voice. 

“Yes. It was very well done,” Pauline replies. “Now, why should we sign on to your book? What about it makes it worth it to agree when it isn’t finished? What does Rory Gilmore have in store for us?”

Rory swallows nervously. “Uh, well, this is a book about me and my mom. My mom and I. She, uh...she had me at sixteen, and…” She swallows, fidgeting with her bracelet. “Sorry. I’m just a little nervous.”

Pauline smiles kindly. “It’s alright. It’s totally normal to be nervous.”

“It’s just like...this was my backup. I was supposed to be a journalist, but you snooze, you lose, you know?” Rory laughs, rambling again. 

Pauline raises her eyebrow again. “You snooze, you lose?”

“I mean…” Rory turns pink. “I didn’t mean this...I didn’t mean this is _ losing, _but it was never the plan. I wanted to be the next Christiane Amanpour, but now I’m just writing some memoir…”

“I think we’ve heard enough for today,” Pauline says, starting to stand up. “Now--”

Rory’s heart speeds up in her chest as she begins to panic. “Wait, if you just--”

“It was nice to meet you,” Pauline says firmly, and Rory knows the conversation is over. “We’ll keep in touch, okay?”

“I…okay,” Rory says numbly. She allows Pauline to shake her hand and to lead her out of the office. The door clicks shut behind her. Rory closes her eyes, pushing back her tears, knowing her face is burning red in utter humiliation.

It’s the same as when she interviewed for SandeeSays, but even worse, because she _ wanted _ this. SandeeSays was when she felt she had gone as low as she could, but this -- she thought she was low before, but she’s deeper than rock bottom now.  
_ I don’t learn from my mistakes, _ she thinks to herself, climbing into her mother’s car and turning it on. _ I just jump the gun and fuck it up every single time. _ She’s utterly humiliated, and she knows it is entirely her fault. If she had just prepared...

Rory knows she hasn’t been herself lately -- for years, really. She doesn’t know when it started, but at some point after graduating from Yale, she started going downhill and hasn’t stopped since. Showing up unprepared to interviews, sleeping with a wookie and an engaged man and cheating and every other mistake she’s made is catching up with her. And the baby...as happy as she’s been this past week, she can’t see any of the positives now. She’s facing a long, lonely road, and she just threw away her compass. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess stops by the Gazette to tell Rory that he’s leaving and to say goodbye, but when he gets there, the atmosphere is completely different than anytime he was here before. Rory sits behind her desk, but she looks upset, which immediately concerns him. 

“Hey,” Jess says cautiously. She looks up from the computer.

“Hey,” she says curtly, before looking back at her computer. She’s not in the mood to chat.

Jess looks at her, puzzled at her tone. He takes a seat in the chair facing her desk. “What’s up?”

She punches a few meaningless keys. “Nothing that concerns you.”

He raises an eyebrow at the coldness in her tone. “Did I miss something?”

“I’m just not feeling like chatting right now,” she says, still not looking at him. She’s frustrated, angry, and most of all, embarrassed -- and she wants him to feel it, too. 

But Jess doesn’t get angry. His tone is too soft, too concerned, and Rory hates him for it. “Rory.”

“What are you doing here, anyway?” She snaps, still not looking at him. She’s humiliated, foolish, and he doesn’t get to see her like this. Not when she’s lower than he’s ever seen her before. 

“I came by to chat, but this seems more important.” He leans forward a bit, trying to catch her gaze. “What’s all this about?”

“Nothing.”

“It’s not nothing.”

“It doesn’t matter.”

Jess sighs. “Rory…”

“Just stop it, Jess!” She exclaims suddenly, startling both Esther and Charlie. “Just shut up and go away! You don’t have to be here just to give me a little pep talk every day! I don’t need your _ help,” _she spits out, bitterness seeping through her voice. 

Jess doesn’t move. “What’s going on?”

The tenderness in his voice is what breaks her. She holds back a sob and pushes out of her chair and runs towards a door off the side of the room. Jess follows her tentatively. He finds himself in the records room, where Rory stands in the middle, trying not to cry. “What’s going on?” He says again. It’s his tone yet again that sends her spiraling. She collapses into his arms, sobbing, and Jess wraps his arms around her. Her body shakes as she cries, holding onto him as tight as she can, as if she thinks she might float away if she doesn’t. And if she’s being honest, she feels that way a lot. Jess is her anchor. She’s always thought that. 

When she calms down, Rory tries to take deep breaths, but it’s hard -- every time she thinks she can, she’s just reminded of everything. “Hey.” She looks up at him. “It’s okay.”

She nods and closes her eyes, focusing on her breaths. He lets go of her slowly, and she takes a step back. 

“What’s wrong?” Jess murmurs. 

Rory takes a shuddering breath. “I’ve been trying to get a publisher,” she explains shakily, “because I’m-- well, it doesn’t matter why. But I only got one interview, and I made a complete fool of myself, and they didn’t even want me because the book isn’t done…” She lets out a sob. “This is just all wrong.”

“What is?” He asks.

Rory sniffs and wipes her eyes. “This wasn’t supposed to happen. I was going to be the next Christiane Amanpour. Traveling the world, writing for all sorts of places…” She shakes her head. “Instead, I’m in the records room of my town’s newspaper crying to my ex-boyfriend.”

Jess frowns. “It’s not all or nothing. You don’t have to be just an author or just a journalist.”

“It’s too late,” Rory sniffs. “I don’t have the experience I should. No one will want me.”

“That’s not true,” Jess argues. “You have a degree from Yale, where you were editor of the newspaper. You worked on the Obama campaign. You’re not giving yourself enough credit.”

Rory shakes her head. “No. No, it’s not good enough.”

“Then focus on the now,” Jess suggests. “Write your book, get a publisher then, and _ then _ try to get a journalism job.”

“Do you really think any legitimate newspaper will hire me after writing a mommy-and-me memoir?”

Jess chuckles. Then, he hesitates before he replies. “You want to work for someone who sees you for your writing skill, not what you write about,” he says. “Someone will want you. You’re only thirty-two. You aren’t out of time just yet.”

Rory wipes her eyes with her sleeve. “Why are you so nice to me?” She asks weakly. “I was taking it all out on you when I wouldn’t even be writing this book if it weren’t for you. You should be yelling at me right now.”

Jess smiles at her, and her heart twinges at the kindness in his eyes. “You know I’m not going to do that.”

“I met Christiane once, actually,” Rory says quietly. “At the Inn. My mom woke me up, and we went over there, and it was incredible. She was so sweet and she gave me her card…” She sighs. “I never used it, though.”

“Why not?”

Rory stares down at her shoes. “I don’t know. I guess I thought I could get somewhere without her help. I wanted to show that I was independent and smart enough to get somewhere on my own.”

Jess nods in understanding. “I get it. You wanted to prove to her and everyone else that you were just as talented. But getting help doesn’t make you weak or any less talented. Just means you can’t always do everything on your own.” 

“When’d you get so wise?” Rory laughs softly.

Jess smiles. “I’ve been around.”

Rory sniffs. “I’ve just been so lost, Jess. I don’t...I don’t…” She swallows, trying hard not to break down again.

Jess rubs her arm comfortingly. “It happens to the best of us.”

“I haven’t been myself in a while now,” she admits, shaking her head. “I used to be driven. I had a goal. I had a dream. And now…”

“Now you’re figuring things out,” Jess says. “I know you’ve made mistakes, but that doesn’t mean you can’t fix this.”

“You don’t know that. You don’t know all the mistakes I’ve made.”

“Try me.”

Rory takes a shuddering breath. “I...I was a freelancer without an agent. That’s such a beginner’s mistake, but I thought I could swing it. And even then, I blew all my money flying back and forth from Connecticut to London to sleep with an engaged man and interview an absent-minded alcoholic. I wasted money and time that I could’ve used to work at something I actually wanted.”

Jess bites his lip, listening to her. Admittedly, Rory feels a bit better getting this off her chest, confiding in him -- a habit she has to learn to break. 

“I fell asleep doing an interview for free on a subject that I didn’t care about. I interviewed for a website that I hated. Did I tell you I slept with a wookie?” 

_ “What?” _

Rory sighs. “I’ve made mistake after mistake and I don’t even know how to begin to fix it.”

“I once felt that way, too,” Jess replies. “But you pick yourself up and you choose a path. You have to ignore your doubts once and awhile.”

Rory shakes her head. “I just want to be Rory Gilmore again.”

Jess softens at that. “So, you will. Pick up a book again. Go find yourself in what you’ve always loved.”

Rory smiles softly at him. “You’re such a good guy, you know that?” She murmurs.

Jess’ eyes crinkle in the way they always do when he smiles. “I think that’s the first time anyone in this town has ever said that about me.”

She chuckles again, and wipes her eyes. The way he’s looking at her is so familiar, carrying a thousand memories and words unsaid, and the weight of his gaze scares her. She looks away, but when she looks back, his eyes haven’t moved. Her heart starts speeding up in her chest as she realizes how close they are, how his hand is still on her arm, how his chest rises and falls with his breaths. She doesn’t move, but continues to look into his warm brown eyes. He starts to lean in, slowly, his eyes closing, but suddenly, it’s too real. Her heart starts stuttering, and she panics, and--

“I’m pregnant,” she blurts out, regretting it the moment she says it. Jess freezes, then straightens himself, blinking a couple times. There’s anger in his eyes, but only for a moment -- it’s gone as soon as it appeared. “Pregnant,” he repeats slowly, as if he was unsure he’d heard her right.

“Yeah,” she says breathily. They both fall silent, and Rory regrets saying anything. She doesn’t know why she did -- she was caught off guard, scared…but it’s not that she didn’t want to kiss him, she realizes. That’s not it. 

Jess frowns. “Who…”

“Logan,” Rory answers, a little too quickly. 

A dark look flashes across Jess’ face. “Huh.”

Rory looks away. “I’m sorry,” she mumbles, her face burning red. 

“No, don’t be,” Jess assures her immediately. “I shouldn’t...I shouldn’t try to...if you’re still with…”

Rory shakes her head. “I’m not with him.”

“Oh.” What was anger in his eyes before has now become something even worse -- hurt. He’s trying to hide it, but she can still see it in his face. His expression reminds her so much of a day ten years ago, with an impromptu trip to Philly and a heart split in two. She hates seeing him like this, but most of all, she hates knowing that she made him feel this way. That she hurt him once again, when he’s done nothing but support her and care for her -- and she can’t tell him that she wants him to kiss her. It’s far too late for that. 

“I’m sorry,” he says, sounding worried, scared. Rory understands. He doesn’t want to lose her, and she doesn’t want to lose him.

“It’s okay.”

“But you’re happy about it?” He asks hesitantly, as if unsure how he is supposed to react.

“Yeah,” Rory confirms. “Yeah, I am.”

To Rory’s surprise, a soft smile spreads across Jess’ face. “I’m happy for you, Ror,” he promises. “This...this is good.”

“You think?”

“I do,” he says. “You’re gonna be a great mom, Rory.”

She feels her face flush red, and she does the only thing she can do -- she smiles. 

Jess gestures towards the door with his head. “Let’s get back out there.”

Rory follows him back into the office, still feeling incredibly awkward and embarrassed. Jess seems to feel similarly, as he doesn’t sit down. “I’m gonna head out,” he says. “This...I’m happy for you,” he repeats. “If anyone can do this, you can.”

“Thank you, Jess,” she murmurs. He nods, turns, and walks out the door. 

Rory folds her hands in front of her and squeezes her eyes shut, mentally cursing herself out for springing the news on him like that. She could still be kissing him right now, she realizes. The thought leaves a bitter taste in her mouth. 

It’s good that he knows, because now, truly, there are no secrets between them. Rory tells herself this, over and over, trying to erase the overwhelming feeling of regret that has been a constant all day. 

It’s not that she didn’t want to kiss him, because she did.

Whatever it was, she has to figure it out soon. 

_ Unless he leaves, _ she finds herself thinking, suddenly terrified that she’s driven him away forever. _ Unless this was what he needed to send him back home. _

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess reprimands himself the entire walk back to the diner. 

Why the hell did he do that? What was he thinking? In what world would that ever be a good decision?

She had been crying -- crying! What kind of person tries to kiss someone who’s just been _ crying? _ He won’t blame her if she is angry. He’s already mad at himself. He can’t _ imagine _ how she could be feeling. 

Through all his frustration and self-directed anger, it stings. It stings because he knows -- he knows without a doubt now -- that she didn’t want to kiss him.

_ There you go, Mariano, _ he thinks. _ You’ve got your answer. _

Maybe he was better off not knowing how she felt. Better off with the hoping and the small moments that made him wonder _ what if. _Because the alternative? It’s so much worse.

This, this is what he’d been trying to protect himself from for years -- this sort of crash and burn with too many casualties to count. Because he’s done this before, twelve years ago in a college dorm, and he thought he’d learned. But here he is, shot down, knowing for sure that his chance is gone. That he’d hammered the final nail in the coffin thirteen years ago when he’d hopped on a bus to Venice Beach. The regret he’d been working so hard to surpass is back, it’s fresh, and it’s not going anywhere any time soon.

_ You could’ve prevented this, _ he reminds himself. _ This is all on you. _

Unsurprisingly, that doesn’t make him feel any better.

He was planning to go, to leave, but now? He can’t. He can’t run away from this. Jess needs to move past his mistake, to prove he’s still her friend, and doesn’t need anything more than that.

But want? That’s an entirely different story. 

**Notes for the Chapter:**

> so...thoughts?


	11. Mars and Venus and Whatnot

**Summary for the Chapter:**

> Rory worries that Jess left, but finds herself having conflicting feelings when she learns he stayed.

**Notes for the Chapter:**

> whoop now we’re feelin the angst

It’s already dark by the time Rory gets home. After Jess had left, she’d stayed at the Gazette office for hours without a break, hoping to distract herself from everything by working. It worked, that is, until she got home. Now, everything is crashing down on her relentlessly. 

“Rory, where’ve you been?” Lorelai calls from her spot on the couch when she hears the front door open and close. “We were going to paint our nails and watch a movie, remember?” She adds as Rory traipses into the room. “Kid, what--” Lorelai begins to say as she turns around, but when she sees the look on Rory’s face, she softens and clambors over the couch to get to her daughter. Rory collapses into Lorelai’s arms, bursting into tears. She chokes out half-formed sentences, like “I didn’t--” and “I can’t--”, unable to speak or think coherently. Lorelai strokes Rory’s hair until her sobs subside. “Let’s sit down,” she says softly, and Rory nods.

“Not a good day, huh?” Lorelai asks once they’re seated.

Rory wipes her eyes with the back of her sleeve. “Not at all,” she says shakily.

“How bad was the interview?” 

Rory takes a deep breath and recounts the events of her interview at HarperCollins to the best of her ability in her current state, unable to look at her mother as she does so. Lorelai lets out a deep sigh.

“Oh, honey…”

“I know.” Rory wipes her eyes. “I just...I…” She shakes her head. “I’ve been so lost. I’ve been lost for years. I thought I was on the road to finding myself, but I don’t know anymore. Who am I? Where do I go from here?”

Lorelai bites her lip. “Only you can answer that question.”

Rory sighs. “I think...I think I lost myself in Logan. And now that he’s gone…” She stares down at her lap. “I’m trying to be my old self again, but I don’t know how to find it.”

“Everyone grows up,” Lorelai says. “Everyone changes.”

“Do you know how long it’s been since I’ve just sat down and read a book?” Rory asks pleadingly. “Like, really fallen in love with one ”

Lorelai clicks her tongue. “You got busy.”

“I know,” Rory says, “but I feel like I just...lost a part of myself. I was talking to Jess, and…” She trails off, cringing at the memory.

Lorelai’s eyebrows raise. “What about Jess?”

“Just another horrible memory of an already horrible day,” Rory laments. 

“Honey, tell mommy what happened with Jess.”

Rory exhales slowly. This all feels much too familiar for comfort. “I went to the Gazette after the interview just to get my mind off of things. Jess came by, and I just...I snapped. I treated him like dirt, taking everything out on him…” She shakes her head. “He didn’t leave, though. He...he just...he just wanted to see if I was okay.”

Lorelai nods. “Seems to be a habit of his.”

“I ran off to the records room, crying…” Rory half-chuckles, but not because anything is funny. “He followed me. I just...I could barely hold myself together. He was there for me, even when I had been horrible to him just the minute before…” She wrings her hands. “But he listened. He listened to me talk about everything on my mind. He doesn’t judge me for all my mistakes, and somehow, he sticks around even when I hurt him...but I don’t know about this time.”

“What happened?”

“After I calmed down, it was...there was a moment,” Rory explains. “And he started to lean in…” She cringes. “I panicked. He tried to kiss me and I told him I was pregnant before he could.”

Lorelai’s eyes widen. 

“But the thing is…” Rory sighs. “I know I freaked out when he tried to kiss me, but it’s not because...it’s not because I didn’t want it.” She closes her eyes and swallows, trying not to break down. “I’m so confused, mom. I thought all my feelings for him were gone, you know? And I thought…” She bites her lip. “I thought he was over me, too.”

“So are you thinking you still like him?” Lorelai asks.

Rory shakes her head. “I don’t know. I’m just so lost and confused and...I mean, he must be, too. We’ve both moved on, but sometimes...I don’t know what came over us.”

Lorelai wraps an arm around Rory, who leans against her mother. “You know, after Luke and I broke up, and I eloped with your father, I was convinced I’d moved on. I thought if I’d put space and time between us, everything would just...go away. But Luke...Luke had always been there. And he had always loved me, even when I thought I didn’t. He was still there for me, even then...these Danes men care a lot about us.”

Rory blinks a couple times before a horrible feeling comes over her. “Oh, god,” she says, feeling sick.

“What?” Lorelai says worriedly.

“I’m so stupid,” Rory groans. “Oh, god.”

Lorelai turns so she can face Rory better. “Kid, you’re scaring me. What realization just dawned on you?”

“I’m a horrible person!” Rory exclaims, standing up and starting to pace. 

“Rory, honey, explain.”

“I can’t believe I didn’t realize…” She shakes her head. “It’s so obvious…”

Lorelai furrows her brow in concern. “What is? You gotta fill me in, kid.”

Rory ceases her pacing. “Jess still loves me,” She says, a knot in her stomach. “And I just threw it back in his face.”

“How’d you get there?” Lorelai asks, but she doesn’t sound surprised. 

“He loves me. He loves me and I...I just hurt him all over again. Why can’t I stop hurting him?”

Lorelai frowns. “Rory. How do you know this?”   
“If...if Logan is my Christopher,” Rory says, resuming her pacing, “then Jess is...is my Luke. And if Luke still loved you…”

“Our lives aren’t the same,” Lorelai points out. “They won’t parallel perfectly.”

“No,” Rory insists. “No, I just...he tried to kiss me,” she groans. “He tried to kiss me, and I...I freaked. He must think...but I don’t even...I can’t…”

“Rory, honey, you’re spiraling,” Lorelai says, climbing off the couch and grabbing Rory from the shoulders. “Snap out of it.”

“I can’t lose him again,” Rory chokes out. “We’re finally friends again, mom. He’s one of my best friends.” Her voice cracks on the word friend. If she’s being honest, the word  _ friend _ doesn’t cover her relationship with Jess at all. Every look, gaze, or exchange carries so much baggage -- fifteen years of it. Fifteen years of heartbreak and almosts and goodbyes carried in one single gaze. She doesn’t know if that can really be defined by  _ friends. _

Lorelai sighs. “This whole guy thing is confusing. Mars and Venus and whatnot.”

“He said he was happy for me,” Rory mumbles. “He told me I was going to be a great mom.”

“Sounds like a good sport,” Lorelai says, rubbing Rory’s shoulders.

Rory presses her lips together. “I feel the same way I did when he asked me to run away with him,” she murmurs. “Saying no even though that’s not how I feel.”

Lorelai hesitates before replying. “How do you feel?”

“I don’t know,” Rory breathes. “I’m too scared to see him. But...I also don’t want him to leave.”

And that’s what it comes down to, the very crux of it all -- Rory’s feelings for Jess and Jess’ feelings for her have always felt undefined, like there’s something there that they both want to ignore. All she’s done is dance around him, push him away when he needed her most, when they were both lost and afraid and alone. And despite that, through it all, they always find their way back to each other, to both build each other up and tear each other down. All she wants to do is fix what she’s broken. But she has a feeling that this time, it’s going to be a lot harder. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess falls back on the bed, exhaling slowly. After leaving the Gazette, he walked around town, trying to clear his head -- but to no avail. He’s still reeling from Rory’s secret, still furious at himself and humiliated and so desperately alone. He wants someone to talk to, but he realizes that the only person he really wants to talk to is her. He loves Chris and Matthew, he does, but his connection with Rory is something that he’s never had with anyone else. 

He’s tired and upset, but he doesn’t think that getting drunk is the best idea, so instead, he calls Chris and Matthew. He knows they’ll just give him an “I told you so,” but it’s better than lying alone with his thoughts. Anything is, really. 

“Dude,” Chris is laughing when Jess picks up, “Dude, shut up, it’s Jess.”

“Sorry,” Jess hears Matthew mutter. “What’s going on?”

“It’s been a real bad day,” Jess sighs. “I needed someone to talk to.”

“Why not talk to the ex?” Matthew suggests. 

Jess bites his lip. “Rory’s pregnant.”

His friends are both silent for a moment, and Jess can only imagine the looks they are giving each other.    
“And I tried to kiss her.”

He expects a smug comment from Matthew or a snarky one from Chris, but all he hears is a long sigh from Chris. “Start at the beginning” is all he says.

Jess recounts the entire trip to the Gazette, beginning with Rory’s sudden coldness to him walking out the door. Once he’s done, it’s quiet again. When Matthew speaks, his voice is much more subdued than usual. “Are you okay?”

“What, no ‘I told you so?’ No smug remarks?” Jess snorts.

“Not this time,” Chris says. 

Matthew clicks his tongue. “Chris is right,” he says. “How are you feeling about all this?”

“I wish I hadn’t done it,” Jess mumbles. “It was better not knowing for sure how she felt.”

“You finally have closure now,” Chris argues. “Maybe this is the first step towards moving on.”

Jess shakes his head, which he realizes is foolish because they can’t see him. “It doesn’t feel that way,” he admits. “I just...there’s always going to be this sense of...of everything being incomplete. And I know she’s pregnant, but she’s not with...with him…”

“Oh, god,” Matthew groans. “The father is that blonde dick?”

“Yeah,” Jess sighs. “But I shouldn’t be feeling anything about that. It’s how she feels that’s important.”

“Come home,” Chris says softly. “Jess, you’re just hurting yourself more. Seeing her every day...that’s going to destroy you.”

Jess closes his eyes. He knows that Chris is right, and he knows that deciding to stay is probably the wrong choice. He just can’t act on it. “I know. But I can’t ditch after this. Not when all I’ve ever done is run away from her.” 

“Dude, stop being a good guy for once,” Matthew begs. “We admire your heart of gold and all that, we really do, but we don’t want to see you hurt like this.”

“But if you really don’t want to leave…” Chris sighs. “We get it. And we’ll stand by you no matter what.”

“Like three peas in a pod.”

“We care about you, man.”

“Like poets care about rhymes.”

Jess laughs. “Thank you,” he says. “God, what would I do without you two?”

Matthew snorts. “Probably be dead in a ditch.”

“You’re probably right,” Jess chuckles. 

“We love you, man,” Chris says quietly. 

Jess can’t help but smile.

-::--::--::--::--::--::--::--::--::--::--::--::--::-

“Come  _ on, _ Rory,” Lorelai begs. “I’m so hungry and I want coffee.”

“We have coffee at home,” Rory insists. 

“Not food.”

Rory crosses her arms. “I don’t want to go to the diner.”

Lorelai sighs. “Rory, honey, you’re going to have to face this eventually.”

“He’s going to be gone,” Rory laments. “He’s going to be gone because of me.”

Lorelai bites her lip. They stand about a block from the diner, after Lorelai had dragged Rory out of the house. But now, she’s refusing to go any further.

“You don’t know that he’ll be gone,” Lorelai argues. “Let’s go and see.”

Rory groans. “Fine.”

Lorelai grins. “You won’t regret it.”

She continues to drag Rory down the street, stopping when they get to the window. Rory peers in, and her heart drops. Lorelai notices the look on her daughters face, and asks confusedly, “What’s with the look on your face? He’s in there.”

She’s right -- Jess is behind the counter as he’s been all month, chatting with Babette and Maury. Rory knows she should be happy that he’s still here, that she hasn’t driven him away, but for some reason, she’s disappointed. And she feels horrible for it.

“Nothing,” Rory replies. But, she doesn’t move.

Lorelai groans. “Come on, you’ve made it this far. Go in.”

“I…”

“Jeez, this really  _ is _ like me and Luke,” Lorelai laments. “How many times have you tried to get me into the diner after a fight with him?”

Rory continues staring through the window. “This wasn’t a fight.”

“I’m not bringing you back any food or coffee.”

“Fine,” Rory concedes. She follows Lorelai into the diner, albeit reluctantly, but follows nonetheless. Jess looks over when he hears the bell jingle, but when he meets Rory’s gaze, she looks away quickly. 

Luke comes out from the kitchen carrying some plates, grinning when he sees the Gilmores. “I’ll be with you in a minute,” he informs them. 

Rory slides into a chair as her mother goes up to the counter. “Hey, Jess,” Lorelai says cheerfully. “Can I have some coffee?”

“Coming right up,” he replies. “You’re awfully chipper this morning, huh?”

“It smells like snow,” she says simply. Jess nods and gets to work brewing the coffee. Rory watches him, feeling guilty. She cannot comprehend why she’s feeling the way she is. Seeing him now only serves to remind her of the day before. Maybe part of her hoped she could run from their problems if he left. And now, she has to face that day and all the ones before it. But even if she’s avoiding Jess’ gaze, his words from the day before still stick with her. She reaches into her bag and pulls out a book for the first time in a while, knowing that doing what she loves is the first step towards finding herself again. She owes Jess everything, she knows this -- she just can’t bring herself to talk to him. 

Jess can’t stop glancing over at Rory, even though he knows he should. The sudden cold shoulder she’s giving him is completely warranted under the circumstances, even if Jess is trying his best to remedy the situation. But if she wants space, Jess will give it to her. He won’t push her, not this time. And while there isn’t a ball to be in her court, he knows that she’ll talk to him when she’s ready. Despite his acceptance of all of this, it still hurts, because there is always a possibility that she won’t want to fix this. That she’s had it with the mistakes and miscommunications, and wants out. That, he would understand, too.

-::--::--::--::--::--::--::--::--::--::--::--::--::-

It snows that evening.

Amidst Lorelai’s cheers and exclamations, Rory finds herself struggling to enjoy this first snow. Lorelai attempts to drag her outside, but Rory stays on the couch, still wallowing in her regret. 

Snow brings hope. It's always been a sign that despite everything going on in their lives, there is still beauty left in the world -- but Rory doesn’t see that as the case this time.

When everything’s falling apart, there’s only a few people she knows she can turn to. And him -- he's someone she can’t stay away from, no matter how much she tries. So while Lorelai is outside, Rory pulls out her cell phone and dials his number.

“Hello? It’s me. Rory.” A beat of silence. “We need to talk.”

**Notes for the Chapter:**

> semi-cliffhanger huh


	12. Who Walks In When I Walk Out?

**Summary for the Chapter:**

> Rory makes a long-awaited phone call.

**Notes for the Chapter:**

> apologies in advance for this chapter being so short -- they’ll rarely be as short as this one in the future, but it gets done what needs to get done ya feel

“Hello? It’s me. Rory. We need to talk.”

“Ace?” Logan asks groggily. “It’s four in the morning here. What’s going on?”

Rory closes her eyes and swallows. “Logan...there’s something I have to tell you.”

She can only picture the worried look on Logan’s face. “What’s wrong?”

“What makes you think something’s wrong?” 

He chuckles quietly -- Odette is probably there, Rory realizes, a sinking feeling in her stomach. He’s trying not to wake her up. Part of Rory wants to just say nevermind and hang up -- she doesn’t want to think about the innocent woman and the man she loves whose lives are about to take a turn. But, no, she’s come this far, and she’s not backing down now. “You’re calling me,” he says, interrupting her thoughts, “at four in the morning, for the first time in a month. Something’s wrong, Ace. What is it?”

Rory wants to tell him that really, nothing is wrong, but she knows that’s not how he’ll see it. She knows how he’ll react when she tells him she’s pregnant. She knows that while it might not be for her, it’s a problem for him -- a dilemma where he’ll definitely take the easy way out. Which is something he’s always loved to do, she thinks bitterly.

“Logan…” She takes a deep breath. “I’m pregnant.”

He’s silent in response.

“It’s yours, but, uh, I guess that…I guess you already guessed that, because I called _ you _...but I told other people already, so, maybe…” She rambles anxiously, perturbed by his silence. “Please say something.”

“I…” He mumbles. “Pregnant, huh?”

“Yeah…”

After another beat of silence, he snorts. “Of _ course. _Of course, this is what I get, right?”

“Get for what?” Rory asks, but she’s sure she already knows what he means.

“Get for-- for _ this, _for not making up my mind, I…” He scoffs. “I can’t believe this.”

Rory bites her lip. She can’t bring herself to reply, nor does she know what to say, even if she could. What she does know is that there are tears in her eyes and a lump in her throat and an urge to cry so strong that she’s not sure she can resist. As much as she expected this, expected exactly this, it stings. It stings more than anything has stung for a while.

“Rory, this is...I’m engaged.”

“I know,” she replies weakly. “I didn’t do this on purpose, Logan.”

She hears movement on the other end -- Logan must be moving to another room. “Do _ what _ on purpose, Rory?” He snaps, his tone less subdued. “Sleep with an engaged man?”

“An affair takes two people,” Rory finds herself saying. “You’re just as much to blame as I am.”

He scoffs again. “I can’t believe this,” he repeats. 

“So, you don’t want to be involved.”

There’s an awkward pause. “It’s going to hold me back, Rory,” he says. “Business is good, so is my relationship with Odette, and--“

“It’s going to hold _ you _ back?” Rory finally snaps. “Logan, you have every resource I could ever dream of! You could do anything, afford anything, whether it’s child support or-- it’s going to _ hold you back?” _

Logan is silent for a moment, stunned at her sudden outburst. “Ace…”

“You don’t want to be involved. And that’s fine, I get it, I do, but that’s it. This-- we’re not friends, we’re not anything. Got it?”

“I’ll pay child support,” Logan offers quietly. “I just can’t--“

“No,” Rory says firmly. “If you want to be out of the picture, you’re out completely. You can see the kid, yeah, they’ll know you’re their father-- but that’s it.”

“Okay,” Logan says. “Okay.”

Rory swallows, doing her best to hold back from crying. “Okay.”

“I have to go,” he murmurs, and with a _ click, _the call is ended.

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess is sitting on the couch, reading, when he hears a knock on the door. He’s thrown off -- it’s ten at night, and everyone in Stars Hollow is usually home by eight -- some sort of unofficial curfew.

He sets his book down and opens the door to find Rory -- a tearful, shaking Rory.

“I called Logan,” she says without prelude, her voice shaky. “And I couldn't find my mom, and I needed to talk, talk about us and Logan and the baby and...and then I realized that the only other person I want to talk about it with is...you.” 

Jess isn’t sure what to say. “You must be freezing,” he murmurs. “You’re not wearing a coat.”

She stares down at her feet, willing the tears away just long enough so that she can get out what she wants to say. “I’m not...I’m not mad at you, Jess,” she chokes out. “What happened yesterday...I get it. It’s okay. I…” She shakes her head. “I called Logan. I told him about the baby, and he...he told me it would hold him back. He got mad, he said this is what he gets for…for…” She lets out a sob. “I…”

“It’s okay,” Jess murmurs, wrapping his arms around her immediately. She melts into him, crying into his shoulder for the second time in two days, relishing in his warm and secure embrace. 

He holds her tightly against him, letting her let it out, both of them unwilling to let go. Above everything else, whether it’s his feelings or hers or anything else you could possibly name, Jess wants her to be okay. He’ll do anything to make sure of it.

When her crying subdues, Jess loosens his grip on her slightly. “Come over here,” he says softly, letting go of her and leading her to the couch. They sit down, and Jess hands her a box of tissues. “Feeling any better?”

Rory blows her nose. “A little,” she says quietly, not quite looking at him. “I’m sorry for coming over like this.”

“I’m not,” he says, reminding himself of an afternoon in Philadelphia yet again -- this deja vu thing is getting to be too much. “I’m always here for you, Rory. That is...if you still want that.”

She looks up at him. “I do,” she mumbles. “I do. I just…” She shakes her head. “I wasn’t sure if it was fair of me.”

Jess smiles softly. “That doesn’t matter. You needed a shoulder to cry on. And I...I just want you to be okay.” 

She smiles back at him, the hesitant look in her eyes beginning to fade. Surprisingly, this doesn’t feel awkward, nor does it feel wrong in any way. That's the thing about the two of them -- no matter how much time and space they put between them, their faith in each other never wavers. It’s still Jess and Rory, Rory and Jess, and absolutely nothing can change that. And in this moment, that’s the one thing that they’re both sure of. 

Rory describes the phone call to the best of her ability, and Jess can’t help but get angry. Angry at Logan, for cheating and for the shitty things he said that have reduced Rory to tears. He knows Rory isn’t blameless, and he’d be lying if he said he wasn’t surprised when she admitted the affair to him -- it wasn’t the Rory he’d known for close to two decades. But he also knows that Rory has a tendency to lose herself in relationships, that she devotes herself completely. And while Jess is glad that she never really lost herself in him, she never really found herself, either -- she’d gone into their relationship with a hang-up and him with one foot in the grave. Even now, now that they’ve found each other yet again in some way or another, things are still different. _ Rory _ is different, as is he -- but it’s so different than what was predicted. 

It’s strange, Jess thinks, handing her another tissue. How this is the opposite of what was supposed to happen. Jess knows who he is, and Rory doesn’t -- and that was never supposed to be the way it went. Rory should be overseas, writing for the New York Times, and Jess should be dead in a ditch somewhere. He doesn’t understand how that’s simply not the case. 

She must be thinking something similar, because she looks away again and says, “I’m at rock bottom, Jess. I’m unemployed, knocked up, and alone. And this…”

“You’re never alone,” Jess says, echoing something her mother had said to her only weeks ago. “You’ve got Lorelai, Luke, this entire town...and me,” he adds tentatively, “if you need me.”

She blinks a couple times. “Thanks, Jess.”

“What are friends for?”

She smiles softly. 

After a moment of silence, Jess stands up. “Let’s get you home.”

Rory allows him to put his coat on her, and they walk in comfortable silence all the way back to her house. Once at the front door, Jess gives her a smile and a nod before turning and walking back to the diner. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory wakes up the next morning with a headache. 

She’d cried a lot the night before as she told her mother everything -- about Logan and Jess and everything in between. 

She pulls herself out of bed and trudges into the kitchen, where Lorelai is brewing coffee. “Hey, hon,” she says softly. “Feeling any better?”

“Not really,” Rory mumbles, rubbing at her eyes. “Couldn’t fall asleep.”

“A lot on your mind?” Lorelai murmurs. Rory nods, sliding into a chair at the table. “Coffee coming right up,” she promises her daughter.

Rory smiles sleepily. “Thanks.”

Lorelai hands her a mug and takes a seat. “How you holdin’ up with this Logan thing?”

“Not great,” Rory admits. “I mean...I expected it. But…” She shakes her head. “It hurt. It hurt a lot.”

Lorelai bites her lip. “I get it, babe.” Beat of silence. “Sorry I wasn’t there for you when you needed me.”

“It’s okay,” Rory says. “I...I had Jess. And while he’s no you…” She sighs. “I don’t know. It’s nice to know that he’s...he’s here for me.”

Lorelai nods. “It is.”

“I just feel guilty. I don’t want to use him like this.”

“You’re not using him,” Lorelai insists. “This is what friends are for.”

“Not like this,” Rory murmurs. “Not the way I treat him.”

Lorelai sighs. “Stop beating yourself up about this, kid.”

“It’s just so weird,” Rory says quietly. “Being close to

him again, after all this time…” She shakes her head. “I need to talk to him.”

“About what?”

Rory bites her lip. “I don’t know. But I’ll figure it out when I get there.”

**Notes for the Chapter:**

> how y’all feelin?


	13. That Damn Icarus

**Summary for the Chapter:**

> After reading some of Jess’ work, Rory can’t help but fly too close to the sun.

**Notes for the Chapter:**

> if y’all don’t mind, pls comment w ur thoughts on the fic so far!!! feedback is always always appreciated  
edit: someone left a long comment and i think either they deleted it or i accidentally did. sorry bro i was boutta reply but then it disappeared

It’s a crisp December morning, and due to the snowfall the night before, the town is nearly buried in snow. Rory doesn’t mind, though, and neither does her mother -- it’s only served to put the Lorelais in a good mood. Due to the snow, Taylor declared it a snow day, so the square is full of kids playing in the snow. Rory watches them as she and her mother head towards the diner, unable to stop thinking about the fact that in a little more than six months, she’ll have one of her own. It’s a strange thought, but not altogether repulsing.

“What’s on your mind?” Lorelai’s voice snaps Rory out of her reverie. 

“I don’t know,” Rory replies with a shrug. “Kids, I guess.”

“Ah, the K word,” Lorelai nods. “You’re still happy about it, though, right?”

Rory bites her lip. “I think so.”

Lorelai nudges her. “Tell mommy what’s wrong.”

Rory chuckles. “Nothing’s  _ wrong,  _ really. It’s just...I’m still not used to it.”

“Used to what?”

“The idea that I’m going to be a  _ mom,”  _ Rory sighs. “Every day I worry more and more that I’m not going to be ready.”

“You will,” Lorelai insists. “I promise.” They fall into a comfortable silence for a few moments.

“What’s with all the banners?” Rory asks, gesturing towards all the snow covered banners hanging around the town square. Kirk is trying to clean one off with a broom, but the only result is more snow falling onto his head. It’s definitely an amusing sight, but it isn’t giving Rory any answers. 

“Dance marathon,” Lorelai replies simply. 

Rory furrows her brow in confusion. “Isn’t that usually in November?”

“Yeah, but the gymnasium was being used for a ping-pong tournament,” Lorelai explains. “Taylor double-booked, so it had to be postponed.”

Rory snorts. “Bet he had some trouble admitting to  _ that _ mistake.”

“Oh, you have no idea.”

“So, you entering this year?” Rory inquires as they near the diner.

Lorelai nods. “I convinced Luke to be my partner.”

“Impressive,” Rory notes. “At least you don’t have to go around begging people anymore.”

“I never  _ begged,”  _ Lorelai retorts. “But, yes, I think we have a real shot at winning this year.”

“Has anyone besides Kirk managed to win?”

Lorelai shakes her head. “Only time was six years ago when he couldn’t enter because he had food poisoning. Otherwise, he always wins.”

“I think you can win,” Rory says brightly.

Lorelai smiles. “What about you?” She asks her daughter. “You planning on entering?”

“Oh, no,” Rory says, shaking her head. “No, I figured I’d just sit and watch.”

“Why not?” Lorelai inquires.

Rory hesitates. While she doesn’t have an elaborate reason for not wanting to participate -- she simply would rather not be standing and awake for 24 hours straight -- she can’t help but wonder if there’s a little bit more to it than that. The last time she went still burns in her mind, vividly, as if it had just occurred. And with everything going on with Jess, maybe it’s best not to dig any more memories up by going. “Just don’t want to,” she says simply, but her shrug isn’t enough for Lorelai. She nods, but Rory can tell she isn’t convinced.

The diner is packed when they enter, which is why Rory is surprised to see that Jess isn’t there helping out. Mature Jess would definitely be there to make sure Luke isn’t too overwhelmed, but he is nowhere in sight. When she inquires Luke as to why he isn’t there, Luke looks up from the cash register. “He’s out with Doula,” Luke explains. “I can get him back here for you, if you want.”   
“Oh, it’s fine,” Rory says hurriedly, “but thanks.” Luke gives her a puzzled look, but nods all the same. Rory shares the confusion -- she wishes she could understand why she’s still nervous to see Jess. It’s not that she doesn’t  _ want _ to see him -- in fact, she plans on paying him a visit later today -- but her mother talking about the dance marathon has thrown her back into a memory that’s a little painful to remember. An argument and a breakup and soft words on the bridge might have been a pleasant memory in another life, but now? It only serves to hurt her just a little bit more. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

“I’ve already started writing my Christmas list,” Doula tells Jess excitedly. “Mom said it’s too soon, but I don’t care.”

“A true Danes girl,” Jess laughs. “What are you asking for?”

The two walk down the sidewalk (or skipping, in Doula’s case) -- Liz asked Jess to look after his sister for the day, and Jess figured he could use a break from the crowded diner, so he agreed. And he doesn’t regret it -- as overwhelming as his family can be, he doesn’t get to see his little sister as often as he’d like. He loves her, he really does, even if she’s a little overenthusiastic for him at times. He’s loved being able to spend more time with her this past month -- dancing with her at the wedding is a good memory, one that is sure to bring a smile to his face. She’s probably his favorite family member, aside from Luke.

“I said a unicorn, but Dad said they’re as real as penguins, so I shouldn’t get my hopes up,” Doula replies dejectedly. “So I guess I’ll just ask for an iPad or something.”

Jess chuckles. “I say stick with the unicorn.”   
“That’s what I said!” Doula exclaims. “Oh, guess what?”

“What?”

“I lost another tooth this morning!” She says happily, grinning widely so he can see.

“Very cool,” Jess replies.

Doula beams. “How old were you when you lost your first tooth?”

Jess pauses to think. “Five,” he replies, “but only because I tripped and fell and knocked it out.”

“That must’ve hurt,” Doula infers wisely.

Jess nods. “Oh, totally.”

“Are you going to the dance marathon tomorrow?” Doula asks suddenly. She’s a very hyper kid, Jess notices -- can’t stick to the same topic for more than a minute.

“I don’t know,” Jess says, shrugging. “Wasn’t planning on it.”

Doula gasps. “You gotta! Mom’s letting me go this year ‘cause she and Dad are gonna be in it, and I don’t want to be by myself.”

“They’re letting you go?” Jess asks, although he supposes he shouldn’t be surprised that his mother is letting his nine year old sister stay up for 24 hours straight. Being conventional has never been Liz’s forte. 

“Pleeeeeeeaaaaaase,” Doula begs, tugging on her brother’s arm. She’s giving him those big, sad brown eyes -- and while Jess is usually pretty immune to her guilt-tripping, his resolve but not be too strong, because he’s seriously considering saying yes. 

He can’t exactly explain to his sister why he doesn’t want to go, because that’s a whole can of worms he doesn’t want to open, and she most definitely will start up the “why?” game. 

Going to the dance marathon is a surefire way to remind him of some now painful memories he isn’t keen on reliving. He doesn’t know if Rory will be attending, but it’s a lose-lose situation. He doesn’t want to be there if she isn’t, but he doesn’t want to be there if she is. Jess has been used to change all his life, but there are some things that just don’t feel right without her, even if her being there will only increase his longing. “Fine,” he concedes, letting out a sigh, but he’s unable to keep himself from smiling when Doula cheers. She launches into a highly detailed speech about her theory on the tooth fairy not being real -- including a testimony from TJ himself -- but Jess can’t get out of his own head. He’s doing it for Doula, he promises himself, but he knows that at least a part of him is being selfish. He doesn’t want to hurt any further, as he knows he inevitably will, but there’s just something so appealing at the same time repelling when it comes to going to the dance marathon. He can’t help but hope, and that’s the most dangerous thing. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess has been in Stars Hollow for a good month now -- a milestone he knows he shouldn’t have let pass, but he figures there might be one good thing about this prolonged emotional hell. While his heart breaks more every day he stays, his inspiration only grows. Maybe all the greats were right when they said what’s bad for the heart is good for the art, Jess thinks. Maybe this is what he’s needed all these years.

While he hasn’t been completely starved for inspiration since he published  _ The Subsect,  _ he hasn’t exactly had an abundance of it, either. But now, after the whirlwind of emotions the past few days have been, he’s been writing for hours on end, spilling out his heart into a document. The word count only goes up.

He’d been thinking a lot about Rory tonight -- ever since Doula practically manipulated him into agreeing to go to the dance marathon this morning, it’s all he’s been able to think about. The last and only time he’s attended the event is still burning in Jess’ mind, which is lucky for him now, because he finally has something to write about.

If Rory can write a memoir, he can too -- and while he’s fictionalizing it somewhat, he’s essentially writing their story. He once told Rory to find what makes her feel so that her readers feel it, too, and he’s wondering why he didn’t take his own advice. Yes,  _ The Subsect _ was in part based on his relationship with Luke and his mother, it wasn’t really about  _ him. _ And he hadn’t allowed himself to make it about _ her,  _ either, even though she is the only person who is able to reach him the way she does. Rory has influenced his life the most out of anyone he’s known, both in good ways and bad. It’s about time he lets himself put it into words. 

There’s a knock at the apartment door that temporarily interrupts his writing flow. Jess blinks a couple times before he stands and answers the door, slowly coming out of his trance. Who he expects it to be, he doesn’t know, but he definitely doesn’t expect it to be Rory at his door. But there she stands, as if conjured by his words, right in front of him. 

“Is everything okay?” He asks immediately, worried based off of a similar situation the night before, but noting that she doesn’t appear to be as distraught as she’d been then.

“Yeah,” she replies. “I just…” She looks away. “I don’t know. I wanted to see you.”

Her words only serve to make his heart twinge, to keep him in the past as long as possible. He knows it’s a sweet sentiment, but everything between them is weighed down by a thousand different memories, both painful and good. “Okay,” he says simply, unsure of where to go from here. He steps aside to let her in.

“Luke told me you were out with Doula today,” Rory mentions breathily, as if she’d run up the stairs. The thought brings a smile to Jess’ face. 

He closes the door and nods. “Yeah. We walked around the square and I took her to the bookshop.”

“How’d that go?”

“She said she’s not a reader,” Jess shrugs. 

Rory gasps dramatically. “And you haven’t disowned her already?”

Jess laughs. “Not yet. I keep telling myself this is just a phase.”

“I don’t know,” Rory says, shaking her head, “Is anybody else in your family a reader?”

“No,” Jess admits. “It’s just me.”

Rory laughs. “Now that’s a shame.” She trails off, unsure of where to go from there. They stand there awkwardly, and Rory looks around until she spots his open laptop. “You working on something?” She asks curiously.

Jess looks back at his computer. “Yeah,” he says anxiously. “But it’s nothing, really,” he adds hurriedly. He wishes now he’d closed it before answering the door. The biggest con about writing about him and Rory is that there’s always the possibility she’ll see it before he’s ready for her to. 

“I doubt that,” Rory snorts. She takes a step towards the desk, but Jess instinctively moves in front of it. As much as he likes sharing his work with her, he can’t show her this, not now. And while he knows that means he may never be able to do anything with this work, that doesn’t even matter right now. He just doesn’t want her to see this, to read it and no doubt realize his feelings for her are still there. Not when they’re recovering from his slip-up only a couple days previous.   
Rory raises her eyebrows. “Someone’s being a little protective.”

Jess leans against the chair. “It’s top secret work, ma’am.”

“Come on,” she begs. “You haven’t published anything since  _ The Subsect. _ I’ve been starved for Jess Mariano writing for years.”

“I just don’t feel like sharing it right now,” Jess explains, biting his lip. It’s not a lie, but it’s not the full truth either -- either way, it doesn’t discourage her.

“Not good enough,” Rory insists. She moves towards the desk, but Jess doesn’t budge.    
“Rory, I said no,” he says firmly, but it’s to no avail. He moves to close the laptop, but Rory is quick -- she snatches it up before he has a chance. She moves away from him, fast, and Jess tries to get it back, but it’s no use. She starts reading, and Jess fills up with dread as he watches the gleeful look on her face slowly turn cold. 

She’s reading his deepest secrets and regrets, all spilled out onto a page, and Jess can’t do anything but watch. She looks up, a little taken aback, and a lot confused. “What is this?”

“It’s…” Jess swallows. “It’s…” But the words don’t come to him. He feels as if he’s used them all up. 

Rory shakes her head. “This...this is about us.” It’s not a question, but a statement -- her tone is knowing, as if something she’s feared has just come true. 

“Rory…” Jess says pointlessly. He knows there’s no point in trying to speak -- she’s already latched onto what she wants to say, and she’ll be damned if she doesn’t get it all out.

“Why are you writing about us?” She demands. Jess feels his stomach drop at her tone. 

Jess looks away, then looks back at her. She’s still staring at him expectantly, awaiting his answer. “I once said that you need to write about what you feel,” Jess mumbles, “and...and this is what I’m feeling.”

Rory blinks a couple of times, surprised at the anger that suddenly surges through her. Her words come out, but she’s not the one saying them -- this is eighteen year old Rory, someone that she’s kept hidden away for over fifteen years, years and years of thoughts finally being said. “You’re still hung up on...this?” She scoffs. “You don’t get to be hung up, Jess.”

His heart drops to the floor. “Rory--”

“No, I get to talk now!” She exclaims, the harsh tone in her voice causing Jess to flinch. “You don’t get to be hung up on this, Jess! You’re the one who -- you’re the one who left! You’re the one who doomed us, and now you think you have the right to sit here and reminisce about the good old days? You don’t! You don’t get to feel anything about this!”

Jess stands there, stunned at her outburst. He processes her words, attempting to quell the frustration it brings up in him. This is an old fight, one he thought they’d put to rest -- but now, he realizes, their lack of closure just means a lack of resolution -- nothing more and nothing less. “I don’t have to run my feelings by you,” he says cooly. “My past is my past, and if I want to reflect on it, I can.”

“No, you don’t!” Rory yells. “Jess, you --  _ you  _ ended this. You lied to me, hid things from me for  _ months,  _ and now -- you forfeit every right to be upset! You  _ left!”  _ Her voice cracks on the word  _ left,  _ which only breaks Jess’ heart more. Despite that, despite how bad he feels and has always felt, he finds himself defensive. She’s not the only one who’s been harboring feelings of resentment. 

“Don’t act like you’re so innocent,” he says coldly. “Like I’m the only reason we didn’t work out.”

Rory gapes at him. “Excuse me?”

“I know I left, Rory -- do you think I didn’t regret that every minute of every day after? That hurting you didn’t torture me for years on end?” He exclaims. “I know I didn’t talk to you, that I hid things -- but I didn’t feel like I could talk to you!”

“How in hell are you pinning this on  _ me?”  _ She demands.

“I’m not…” He trails off dejectedly. “No one gets sole responsibility, and that’s my point. You entered our relationship while you were still in love with Dean. All I ever heard was Dean this and Dean that, because I was right, that it  _ always _ came back to Dean! You didn’t want me, Rory! You wanted him!” 

Rory looks at him incredulously. “Of course I wanted you! But you wouldn’t let me have you!”

“It was always that Dean wouldn’t do this, or why couldn’t I be more like Dean,” Jess retorts angrily. “You couldn’t take my word that I didn’t fight him, you couldn’t -- you were still hung up on him!”

“I wasn’t!”

“Then why did you get together with him only a  _ year _ after I left?” Jess demands.

Rory blinks a couple times. “I...I…”

“You were still hung up on him!” Jess repeats himself. “I know I was insecure, but god, didn’t I have reason to be? Everyone in town preferred him -- including you! Everyone loved him, thought he was better for you, that I was just a bad-boy phase or rebound! I knew I would never be accepted as someone you chose -- and only because Dean broke up with you!”

“That’s ridiculous!” Rory shouts back.

“No, it’s not!” Jess scoffs, feeling tears press at the back of his eyes. “The one person I depended on to care about me, to be there for me, to want me for who I was couldn’t even do that.”

Rory shakes her head. “It is not my fault that you left.”

“That’s not what I’m saying!” Jess exclaims, exasperated. 

“Then what  _ are _ you saying?” She demands. “You were a  _ coward, _ Jess, for running like you did. You were so angry at the world that you didn’t even care who you hurt, so absorbed in all your exaggerated angst that you couldn’t think about anyone but yourself. You were a  _ coward,”  _ she spits, venom dripping from her words. “You still are.”

Jess swallows, refusing to break down. He’s stunned at how cruel her words are, how hideous Rory’s words can get if she lets them, but he can’t just leave it at that. He can’t let her reduce him to nothing. “You refuse to accept that you did anything wrong because you let everyone convince you that you were the most important, precious little thing in the whole world,” Jess retorts. “You were spoiled, Rory, so spoiled that you didn’t even stop to think that maybe you hurt me, too. But I guess that’s just how you are.”

Rory blinks a couple times, her breathing short and fast. “Screw you, Jess,” she spits. “Screw you.” And with that, she turns on her heel and storms out, the door slamming shut behind her. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

“Ready to order?” Lorelai asks when she hears the door open and slam shut. However, when Rory stomps into the room, her grin fades. “What’s going on?”

“I need a partner for the dance marathon,” Rory announces, sounding determined. 

“What changed since this morning?” Lorelai asks, confused. “What just happened?”

Rory dismisses the question. “I need a partner,” she repeats. “Got anyone in mind?”

**Notes for the Chapter:**

> hmu on tumblr (xliterati) or ig (literatily)


	14. Death By A Thousand Cuts

**Summary for the Chapter:**

> Rory and Jess both attend the dance marathon, only to find themselves fighting the same battle.

**Notes for the Chapter:**

> this chapter has scenes that i had had in my notes for ages and i’m so glad it’s finally done and ready to share. good luck

“It’s so early,” Rory complains, traipsing slowly towards the school, arm in arm with her mother.

“Hey, no kvetching,” Lorelai scolds her. “You signed up for this.”

Rory yawns in response.

If she’s being honest, Rory isn’t sure that deciding to sign up for the marathon at the last minute was such a good idea. Being awake for twenty-four hours probably isn’t the brightest decision, but it doesn’t matter anymore -- she isn’t about to back down now. She’s angry with Jess, and she _ wants _to make him jealous -- no matter how childish it seems.

“Is he almost here?” Rory moans.

“I don’t see -- oh, he’s right over there!” Lorelai exclaims, gesturing over to a young, unfamiliar face. The man walks over with a hesitant smile.

“You’re Rory and Lorelai?” He asks tentatively.

Lorelai nods. “This is Rory. Rory, this is Adam, your partner.” Rory waves weakly. 

Adam grins. “Nice to meet you, Rory.”

When Rory stormed into her mother’s house the day before, determined on finding a partner, Lorelai had taken it upon herself to scout out the most talented, most handsome partner that you can get on a 12-hour notice. And, Rory will admit, she didn’t do half bad. 

She smiles weakly. “I’d shake your hand, but if I let go, I think I’ll fall over.”

“Not a morning person, huh?” He asks, chuckling.

Rory shakes her head. “Not at all.”

Luke catches up with the group, holding two thermoses. “Here,” he whispers, shoving them at Rory and Lorelai. “You didn’t get these from me.”

“Thank you, thank you, thank you,” Lorelai says gratefully, holding the thermos close to her chest. “Oh, coffee, mommy will never leave you again.”

“Shall we check in?” Adam asks Rory, eyeing Lorelai amusedly. Rory nods, and slowly releases her grip on her mom. “See, you didn’t fall over,” Adam laughs as he follows Rory to the check-in, where Babette sits behind a table. 

“So, I haven’t seen you around much,” Rory says as they walk into Miss Patty’s once they’re done checking in with Babette. “Are you new to town or am I just really self absorbed?”

Adam nods. “I moved here fairly recently,” he explains. “Lily and I move around a lot, and we decided to stay in Stars Hollow for a little while before we go to Asia.”

“And Lily is…”

“My daughter,” Adam replies. 

“And her mom is okay that you’re doing this?” Rory asks worriedly, remembering her mother’s unfortunate encounter with Mrs. Appleman. 

Adam laughs. “There’s no mom in the picture, but I don’t think _ anyone _ likes their partner getting up at five in the morning.”

“Sorry about that,” Rory says sheepishly. “I know it’s last minute.”

He shrugs. “I’ve been wanting to see one of these wacky town events, anyway. No harm, no foul.”

“Just be prepared for the runaround,” Rory warms him.

“The _ what?” _

Once their physicals are complete, they leave and head into the gym. Rory opens her thermos and takes a large swig. 

“Nothing says coffee like six in the morning, huh?” Adam notes.

Rory grins. “Definitely.”

“So, why did you need a partner on such short notice, anyway?” Adam asks curiously. “Most people signed up ages ago, right?”

Rory hesitates before replying. Adam is nice, and she doesn’t _ not _ trust him, but how much does she want to tell a stranger? How deep can she go about the _ real _reason she’s dancing with him, and the one person she wishes she was with instead? “No reason, really,” she finally replies, shrugging, but she can tell that Adam isn’t convinced. 

They continue to chat until Taylor announces into his megaphone that there’s five minutes to go until the marathon begins. “You ready?” Adam asks.

Rory nods grimly. “Not thrilled about the moving part of it all, but it doesn’t get more ready than this.”

The doors open, and in walks Doula -- with who else but Jess. Rory turns her head at the sound of the doors opening, only to look away quickly when she sees who it is. She glances over through the corner of her eye to see Jess and his sister say hi to Liz and TJ, who are competing. They sit down on the bleachers, and Jess meets Rory’s gaze for only a moment -- she averts her eyes immediately. 

The horn sounds, and the swing band picks up -- the marathon has officially begun. Rory finds herself having a much better time than expected. For a while, a long while, she doesn’t even _ think _ about Jess -- she’s forgotten how fun this is, how nice it is to dance around with the whole town. But then, she dances past _ him _, and it all comes rushing back.

Adam must notice the change in her expression, because he frowns and says, “Okay, what’s the deal with you and that guy?”

“What guy?” Rory asks innocently, trying to feign confusion.

Adam doesn’t buy it. “The guy that’s been staring at you and you keep looking over at for the past hour.”

Rory bites her lip, unable to glance behind her at Jess. “It’s nothing, really.”

“I call bull,” he replies. “Now, I’m happy to play the role of ‘jealous boyfriend’ to get you to talk about it, but wouldn’t it be easier if you just told me?”

“So, you like to travel, huh?” Rory says instead, hoping it’s enough to change the conversation and keep it there.

“Rory.”

She lets out a sigh. “It’s just a really long story, okay?” 

“Good thing we’re here for twenty-three more hours,” Adam replies simply. 

Rory hesitates for a moment. “Let’s move over there,” she says, hoping to get out of Jess’ earshot.

“Okay, now, spill,” Adam insists. 

Rory exhales slowly. “He’s a...an ex,” she finally says, but her voice catches on the word _ ex. _ Just like calling him a friend, identifying Jess as an _ ex _ doesn’t quite fit. They used to date, yes, but it’s so much more than that. _ They’re _ so much more than that. There’s a deeper connection there that just can’t be covered by such a small, simple word.

Adam whistles. “An ex.”

“Yeah,” Rory breathes.

“Tell me the story.”

Rory recounts her history with Jess, the whole thing, starting from the moment they met to last night. Adam listens intently, and Rory finds herself grateful -- grateful for him and grateful for the weight that’s lifting off her chest. She doesn’t let herself talk about this all that much. In fact, her fight with Jess had been the most she’d said about their past in a long time.

“That’s a doozy,” Adam says when she’s done talking. “And now, you’re trying to make him jealous?”

Rory flushes. “It’s childish, but…”

“Maybe, but it’s understandable,” Adam replies. “Seems like there’s a really loaded past between you two.”

“Yeah,” Rory nods. “There is.” They fall silent for a moment. “Thanks for listening,” she says softly.

Adam smiles. “Hey, what are jealousy decoys for?”

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess can’t stop watching Rory. It’s a bad habit, and he wants more than anything to break it, but even when talking to his sister, it’s next to impossible to ignore her.

She’s dancing with someone Jess hasn’t seen before -- although that doesn’t mean much, because he doesn’t visit Stars Hollow often enough to recognize every face -- but it all feels way too familiar. He knows that isn’t Dean she’s dancing with, and he’s with Doula, not Shane, but there’s a part of him that thinks she’s trying to make him jealous, just like the time before. 

He’s _ not _ jealous, not really -- Jess doubts she has any sort of romance going on with this guy, and even if she did, he tells himself it wouldn’t matter. If this rift between him and Rory goes on much longer, he won’t be in Stars Hollow for more than a few days longer, anyway. There’s no reason to stay if the girl he loves doesn’t really want him there at all. 

“You look sad,” Doula points out suddenly. “Why do you look sad?”

Jess looks at her. “I’m not sad. See?” He grins widely and points at it.

Doula giggles, but then she shakes her head. “You’re sad.”

“Doula, I _ promise _ you, I’m not.”

“Daddy says not to lie,” Doula says wisely. “Unless you _ really _want to.”

_ That sounds like TJ, _Jess thinks to himself, amused. “It’s grown-up stuff, okay?”

Doula pouts. “I’m nine. I’m almost a grown-up.”

Jess chuckles. “Oh, yeah?”

“Who’s the girl you keep looking at?” She asks, pointing towards Rory. 

Jess sighs. “That’s Rory. You’ve met her, she’s Lorelai’s daughter.”

Doula scrunches her nose. “Who’s Lorelai?”

“Uncle Luke’s wife.”

“Oh, I know Rory!” Doula realizes suddenly. “Yeah, she helped me tie my shoes once.”

Jess nods. “That’s her.”

“Why do you keep staring at her?” Doula inquires.

Jess eyes her warily. “How much do you already know?” 

Doula shrugs. “I dunno. You guys are friends, right?”

Jess lets out a sigh and looks back out at the dance floor. As wacky as the Danes family can be, Jess never really leaned into the whole eccentric deal. He’s happy to talk to Doula about most things, really, but this -- discussing his ex-girlfriend with his nine year old sister seems to be crossing a line that he drew for a reason. The only people Jess has opened up to about Rory are Chris, Matthew, and Luke -- Doula doesn’t exactly fit the general trend.

“You could say that,” he finally says, and leaves it at that. 

Doula scowls. “No one tells me _ anything,” _she pouts, overdoing it on purpose. 

Jess looks at his sister and shakes his head in amusement. “You’re a master manipulator, you know that, right?”

She simply grins.

Jess sighs and shakes his head. He thinks remorsefully about the book in his back pocket. _ I’ll get to you later, Faulkner. _“There’s not much to tell,” he says. “I used to...I used to date her.”

“Why aren’t you still together?” Doula questions him. 

Jess hesitates. “Sometimes, things just don’t work out,” he says slowly. “This was just one of those times.”

Doula must sense that that was the extent to which Jess is willing to open up, because she doesn’t press on -- instead, she changes the subject, inquiring as to why and how he could possibly love reading. “It’s boring,” she insists. “How can you do it all the time?”

Rory is still dancing with the guy Jess doesn’t know, laughing about something or other while the guy grins. Jess still isn’t _ jealous, _ not at all -- he’s smart enough to know that this guy isn’t her boyfriend, isn’t anything more than a friend. And yet, it’s never been below Rory to try to make Jess jealous, either. He’s _ not _ jealous, he keeps telling himself, but he does wish she was over here with him or he over there with her. Not _ instead _ of that guy, not _ replacing _ anyone -- he just wants Rory. But she’s mad at him, and honestly, he can’t blame her, even if he wishes he could. He’s so angry with himself, and has been for thirteen years, so this is long overdue. He once said _ it is what it is, _her and him, and he stands by it -- but watching her now he feels their divide only grow wider, serving to destroy any ounce of hope that he had left. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory can’t ignore Jess. She’s been trying, fighting to keep her gaze averted, but it’s no use. Adam seems to take notice, because he raises an eyebrow at her and says, “So, you’re still thinking about the ex, huh?”

Rory sighs. “I wish he would just go away.”

“No, you don’t,” Adam says. “You still have feelings for him, don’t you?” When Rory remains silent, he sighs. “Let me ask you a question. What were you trying to accomplish tonight?”

Rory bites her lip and looks over at Jess. He has an open book in his lap, but he isn’t reading it -- instead, his gaze locks with hers, right before she immediately looks back at Adam. “I just...I wanted to make him mad,” she admits. “I wanted him to feel as hurt and angry as I felt when he...when he left.”

“And you think that’s the best solution?”

“I don’t know,” Rory admits. “I never...I never know what’s right without him.” 

Adam nods grimly. He looks over at Jess, then back at Rory. “What are you going to do about it?”

Rory knows he’s right. She knows somewhere deep down that she always finds herself in Jess, that she always comes back to him, hoping he’ll set her straight. And while she’s grateful for him, the thought now stirs up an anger in her she hadn’t seen coming. She’s mad, mad that she feels so lost without him, that he left and she still can’t let go. Angry that he hasn’t been able to, either. And most of all, she’s angry that he found who he was without her. 

Rory can’t deal with the weight of his gaze fixed on her. She wants him to stop, to go, to do _ anything _ else other than look at her. But Jess doesn’t look away. 

They continue to dance, ending up right by Jess and Doula. Rory meets Jess’ gaze for what feels like the hundredth time, and all her anger hits her, hits her hard, without warning. She looks at Adam and shakes her head. “I’m just so...so angry,” she mutters. “That he won’t go. That I can’t…” She looks over at Jess and speaks again, this time directed towards him. “Would you stop staring?”

Jess nudges Doula. “Hey, why don’t you go talk to Sookie’s kids?” She nods and hurries off. He then faces Rory, and says, “I could say the same to you.”

It all feels so familiar -- it’s nearly the same fight they had fourteen years ago, but Rory can’t stop herself from following the footsteps of the past. “Why are you even here?”

“I have a life outside of you,” Jess snaps. “I’m here with my family.”

Rory scoffs. “You just sent your sister off the second I spoke to you.”

“Because I didn’t want her to see us fight,” Jess replies evenly. 

“Just get out of here!” Rory exclaims. “Leave. It’s your favorite thing to do, isn’t it?” She knows she’s being cruel, and she’s aware it’s unnecessary, but she doesn’t care, not now in the moment. She says it all the same. 

Jess doesn’t flinch. Instead, to her surprise, he softens, and the pure regret and tragedy in his gaze is enough to break her. Rory lets out a sob and pushes away from Adam, running out the double doors. Jess immediately gets up and goes after her, pushing through the double doors and out into the town square. 

“Why do you keep following me?” Rory exclaims, turning on her heel to face him. “Why won’t you leave me alone?”

“Because I won’t let us leave it like this again,” Jess says breathlessly. “Leave _ us _ like this again.” When Rory stays silent, he continues to speak, his voice softer. “Now, if we need to talk about this, then...then we will. But I don’t want to run from it anymore.”

Rory finally wills herself to really look at him, to really see what he’s feeling. His face is pained, something so similar to what it was fourteen years ago on the same night, and it breaks her. “We were going to be _ happy, _ Jess,” she says, her voice cracking on the word _ happy. _He stays silent, unable to reply, so she continues. “We were going to be happy.”

Jess blinks a couple times. “You thought about our future?” He asks softly, his voice broken and hopeful all at once.

Rory furrows her brow. “I mean, didn’t you?”

Jess looks away and then looks back, only reminding Rory more of the night she’s been running from for so long. “I did.” His voice is so quiet, nearly silent -- but she hears him. She hears him, and that’s what matters. 

“Well...I did, too.”

“What was the plan?” Jess murmurs.

Rory swallows, trying to keep herself composed. After all the years of hiding and running and hoping, they’re here -- and it’s still not where she wants them to be, or where he wants either, but it’s something. It’s something, and she doesn’t want to lose it. But looking into his eyes scares her still -- there’s something so vulnerable and tender in his gaze that makes her so unsure of what she wants. “Plan?”

Jess chuckles softly. “Come on, I know you had a plan. You’re Rory, you must’ve had one. Tell me.”

Rory fiddles with her hands anxiously. “I mean, it wasn’t really a _ plan _ plan, just stuff I thought about…”

Jess doesn’t look away. “Tell me,” he says again. 

Part of Rory wants to run, run away as fast as she can, leave all this behind and never face this. Never face _ him. _It’s easier, so much easier to pretend his feelings aren’t there, and that hers aren’t either, and that this whole time, this entire month he’s been here, they’ve been friends and nothing more. It’s always been so much easier that way. And yet, she opens up -- slowly, yes, but she’s letting him in. After all this time, she’s letting him in. “We were gonna travel,” she murmurs, her face flushing pink. 

“Yeah?” 

“Yeah,” she breathes, feeling a little emboldened at the look on his face. “I mean, first, I’d...I’d graduate, you know, right -- go to college, all that. I imagined...I pictured us living together, maybe my junior year, in New Haven…well, obviously New Haven, that's where Yale is...” Jess smiles at her rambling. “You remember when I told you about the schools I got into?”

He nods. 

Rory smiles softly. It’s a good memory, one she hasn’t let herself uncover in a good while. The way the grin spread across his face, how he picked her up and spun her around, then kissed her and told her how proud of her he was...it was a rare moment where he was truly open, not hiding anything...why had she forgotten?

“The apartment would be really small and crappy and stuff would break _ all _the time, but...but we wouldn’t mind,” she laughs softly. “And...and after I graduated, we’d travel. Starting in Europe, then Asia, Africa, Australia, South America...and then home.” 

“No Mexico?” Jess asks, his voice low.

Rory shakes her head. “Please. I’m forever scarred from Lane’s honeymoon stories.”

“What else?” He prompts her.

Rory tucks some hair behind her ear. “We’d, uh...we’d move to New York. After we got home.”

“Better apartment?”

“Totally.”

“Lots of books?”

“Tons,” Rory agrees. “Like, wall to wall shelves.”

Jess smiles and bites his lip. “I could live with that.”

“And...and I -- maybe...I thought we’d live there for a few years, because it’s way easier to be a writer in New York than in Connecticut. You’d get a book deal, and then I’d be hired by the New York Times. And I…” She trails off.

“Sounds really nice,” Jess murmurs. 

There’s a moment where neither of them speak -- where they look at each other and then look away, open their mouths to speak and then close them, both unable to put what they want into words.

Jess finally speaks, and when he does, his voice is low and gravelly. “I thought our story was...was one for the ages, you know?” He says. “You, and me, always coming back to each other, finding each other again and again through the years despite it all…” He shakes his head. “I…”

He falls silent for a moment, searching Rory’s eyes for _ something, _ just for the slightest sign of reciprocation. The look on his face terrifies Rory -- the unrestrained emotion, the pain, the years of heartbreak all directed at her. 

“I…” Jess takes a deep breath and exhales slowly. “I still love you, Rory.”

His words cause tears to well in Rory’s eyes, and she finds herself choked up -- but for all the wrong reasons. These are words she hasn’t heard from in a long, long time, and in any other scenario, she might’ve been happy to hear them. But now, it just feels too little and too late. 

“Just go, Jess,” she chokes out pleadingly. “Just go.”

A thousand emotions flash across Jess’ face at once. Then, he smiles sadly, nods, turns, and walks away. 

**Notes for the Chapter:**

> i do not know why i do this to myself


	15. Goodbye Doesn’t Mean I’m Gone

**Summary for the Chapter:**

> Rory is dismayed to learn that Jess left for Philadelphia.

**Notes for the Chapter:**

> for the full experience i recommend listening to she used to be mine at the third section

When Rory wakes up the next morning, for a split second, she’s fine. It’s sunny outside, for the first time in days, and the heat has finally been fixed in her bedroom -- but then, all her memories from the night before come crashing down on her all at once. She stifles a sob and forces herself out of bed. She doesn’t want to cry first thing in the morning, even if thinking about Jess and their fight and the words he’d said to her makes her want to do just that.

She steps into the kitchen to see Luke and Lorelai sitting at the table, talking in hushed voices. They turn to look at her, and the grim looks on their faces cause Rory’s stomach to drop.

“Jess is gone,” she guesses immediately, and when Luke and Lorelai’s expressions don’t change, she knows she’s right. 

Lorelai sighs. “Yeah.”

Rory swallows, this feeling all too familiar. “He didn’t say goodbye.”

“We, uh…” Luke grimaces. “I went to the diner and the apartment was empty. All his stuff is gone.”

“We didn’t know if we should tell you,” Lorelai adds, pity evident in her voice. “I didn’t want you to--“

“I don’t need to be protected!” Rory suddenly exclaims. All her anger towards Jess, towards herself, spikes before she can calm it. “I’m not a teenager anymore! I can handle it!” She stares down at her shoes and swallows. “...and it’s my fault he’s gone, anyway.”

“Rory, that’s not--” Lorelai begins, but Rory cuts her off.

“I told him to go.”

Luke furrows his brow in confusion. “Why--”

“He, uh…” Rory bites her lip. “He told me he still loved me.” Beat of silence. “And I told him to go.”

Lorelai’s eyes widen, but she stays silent. Luke’s grim expression remains. Rory exhales slowly, her face flushed pink. Telling Jess to leave after he spilled his heart out to her is not something she’s proud of, but she doesn’t know what else she could’ve done, other than just stay silent. Rory _ knows _ Jess would never get mad at her for not saying it back -- she’s aware how hard it’s always been for him to say it -- but she can’t say she loves him. 

It’s not that she _ doesn’t _ \-- but Rory can’t put how she feels about him into words. Not now, not yet -- not when she finds out he’s left like this. Not when she’s missing him with the wound still fresh. Jess being gone isn’t something new -- but she’d gotten so used to him being around that now, it feels more wrong than ever. 

“Guess you can hate him again,” Rory says to her mother with a bitter chuckle. However, Lorelai shakes her head.

“Not this time, kid,” she says, to Rory’s surprise. She never thought Lorelai’s fondness regarding Jess would last. _ How can I hate anyone that loves you like that? _ Is what Lorelai wants to say. Instead, she says, “I think you two will be okay.”

Rory wishes she could be so sure. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess’ apartment feels empty at first.

It’s possible he’s just projecting -- the hole he feels in his heart is overwhelming him, threatening to swallow Jess completely. He hasn’t been able to get his mind off Rory the entire ride up, and now he’s entering his studio apartment at two in the morning wishing she was there with him. Leaving her behind is the hardest thing, leaving her there with his weighted words and broken heart without any reply -- but he’s laid it all out for her, and there’s nothing more he can say.

He drops his keys on the counter, and rubs his eyes as he flips on the light switch. When he opens his eyes, he jumps back a bit in surprise. “Chris? Matthew? What are you _ doing _ here?”

“You gave us a key,” Matthew replies, mouth full of chips.

“For emergencies only,” Jess points out. “It’s two in the morning. Why aren’t you guys home? And why are you sitting in the dark?”

Chris frowns. “We could ask you the same thing. Why are _ you _ here at two in the morning?”

“Yeah,” Matthew agrees. “Why didn’t you tell us you were coming back?”

Jess exhales slowly, drumming his fingers against the back of one of the chairs at the table where his friends are sitting. “It was...last minute.”

“Dude, you look exhausted,” Chris says, concerned. “Sit down. You must’ve been up for hours.”

Jess does as Chris says, sliding into a chair. “What’s wrong?” Matthew asks. “As in, what sent you driving to Philly in the middle of the night?”

Jess shakes his head. He’s been spilling his heart out to his friends a little too much lately for his taste -- opening up to other people has never been his favorite pastime. And tonight, the wound is all too fresh. “I don’t want to get into it,” Jess says huskily. “It’s been a long night.”

Chris and Matthew exchange worried looks. “Jess--” Chris starts, but Jess cuts him off. 

“Stop!” Jess exclaims. “Just...stop, _ please.” _ His voice cracks. 

Chris sighs. “I know you don’t like talking about this shit, but you look like a wreck.”

Jess snorts. “Thanks.”

“Consider it as us repaying you for using your apartment to hang out in for the past month,” Matthew adds.

“You _ what?” _

“Besides,” Matthew continues, “you’ve always been there for us, Jess. Let someone else take care of you for once.”

Jess shuts his eyes and swallows, feeling the same urge to cry he’s been feeling all week. “I messed up,” he says weakly. “I…” 

He recounts the happenings of the past few days, starting from Rory coming to him about Logan to her telling him to leave. When he’s done, the three of them fall into uneasy silence, until Matthew breaks it. “God, that’s a lot.”

Jess snorts. “You don’t say.”

“I’m sorry,” Matthew says. “I am. This just...it sucks.” Chris nods in agreement. 

Jess shakes his head. “It’s my fault. I was pushing it by staying there, but I just…” He sighs. “I couldn’t get myself to leave her, you know?”

“You’re an artist. Breaking your own heart is second nature,” Chris suggests.

Jess raises his eyebrows. “No reprimanding?” 

Matthew shakes his head. “Nah, we can’t blame you for this.”

“I shouldn’t have told her,” Jess says. “It wasn’t right. I just thought...I thought that maybe she...she felt the same way. But I guess I should’ve known better, all things considered.”

“You couldn’t have known what she was going to say.”

“But it was too risky,” Jess laments. “It’s too little and too late. I need to let go.” His voice is choked and on the verge of breaking. “I should’ve let this -- _ her _ \-- go when I left the first time.”

Chris taps his fingers on the tabletop absentmindedly. “Jess…”

“I gave any chance with her up the _ moment _ I got on that bus thirteen years ago,” Jess says shakily. “To think anything else is…”

Matthew stands up suddenly, the chair squeaking against the wooden floor. “Okay, we’re watching a movie and eating our feelings,” he decides. “Good thing we brought ice cream here a week ago.” 

Jess chuckles and wipes his eyes with the back of his hand. “Alright. But I don’t have that many movies and the only streaming service I have is Hulu.”

“The fact that you don’t have Netflix is appalling,” Matthew says, already going through Jess’ collection. “Truly appalling.”

“Starving artist or something like that.”

Chris laughs. “Something like that indeed.”

“If you think me having DVDs is bad, you should see Rory’s--“ He cuts himself off. Chris and Matthew pretend not to notice. 

Jess might still be hurting, but he also has his friends -- and while he goes to sleep that night still upset and wakes up to an empty apartment and an empty bed, he doesn’t know what he would’ve done if they hadn’t been in his apartment at two in the morning without his permission, right when he needed them most. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

A week passes before Rory is able to write again. 

Well, she _ could _ have written -- her laptop was fully charged and in perfect condition, and with no best friend available, her schedule was wide open, but getting herself to write -- that was the hardest thing. 

With Jess gone, so was Rory’s motivation. And now, a week has passed, and she’s only now forcing herself to sit down and open her laptop. She briefly wonders what Jess is doing right now -- if he’s working, out with friends, or with a girl. She quickly banishes the thought from her head and focuses on the task at hand. 

The document is already open, but Rory’s heart sinks when she realizes what part she’s at. When Jess was there, writing about their relationship hadn't been a problem -- which makes her feel guilty as she recalls how she’d reacted to Jess writing about them -- but now, she’s at the beginning of the end. The fights at the party, his disappearing act, all waiting to be spilled out onto the page like a confessional. This book is about Rory and her mother, yes, but her relationship with Jess affected all of her relationships. It still does.

She considers skipping it, coming back to that part later once the wound has healed -- but she knows there’s no use. She doubts this will ever stop hurting, not until there’s a resolution and closure, and with Jess gone, that won’t be happening any time soon. There’s no point in leaving it for later -- at least she’s been thinking about it all week. 

But once Rory starts writing, she finds it easy -- all her unresolved feelings are coming back to the surface, ones she thought she’d killed ages ago. 

She hadn’t let herself have a Jess box, and that she regrets -- any thought or memory of him was strictly banished, and she had been set on acting like he’d never been part of her life at all. It was a mistake, and she knows that now. 

Just like she’d told him on that final one-sided phone call, she didn’t pine. Or, rather, she hadn’t let herself, because those memories weren’t gone, only delayed. After burying her pain so deep, Rory can only now examine it, thirteen years too late. 

She told Jess she might have loved him, and looking back now, Rory knows she did. She loved him, loved him completely, loved him despite all those problems he couldn’t seem to face. She’d blamed him for it then, nearly hated him for being so troubled and being unwilling to discuss it. But she understands it now. Jess had his demons -- an abundance of them, really -- and they’d been too much for an eighteen year old kid. He was never one to talk about his feelings, and it took him that long to tell her how he really felt, so she can imagine how difficult it would have been for him to tell her about his problems, especially after the hole he dug for himself. 

Only a couple days earlier had he told her that he had felt as though he couldn’t talk to her, and while she’d resented that in the moment, she realizes now that he was right. She’d been there for him in other ways, sure -- a hand to hold, lips to kiss, someone to discuss literature endlessly and whatever else was going on around them. But she had high expectations for him, expectations that aligned too much with how Dean had been, and that weighed on Jess heavily. 

Back then, Rory let everyone convince her that Jess hadn’t been good to her, that she hadn’t been happy, but it wasn’t true. She knows that now. She knows that it was only bad at the very end, where his secrets had caught up to him and she’d walked out of that bedroom door and cemented their fate. 

It’s not her fault entirely, but she’s only now coming to terms with the fact that the same goes for Jess. Why she let everyone make her think it was, she can’t comprehend -- Jess didn’t treat her like dirt, not at all. If anything, he treated _ himself _ like dirt, and it broke her to see it. And his jealousy, his anger towards Dean, his anger towards her mother, his anger towards _ her _\-- she thinks she understands it now.

Jess definitely could’ve handled things better, there’s no doubt about that -- but Rory realizes she could’ve, too. It’s a realization that’s long overdue. Taking responsibility for her actions has never been a strong suit, but somehow, it’s gotten worse. 

These past years without him, somehow, Rory lost herself. Lost herself in Dean, lost herself in Logan, lost herself in her own self-doubts and insecurities. And she realizes now, she’d never been so sure of herself than when she was with Jess. Deciding to go to Yale, striving towards her dream of being a journalist, whatever else -- he’d never been in her way. He loved her, and he showed it, even if it wasn’t in the most obvious way.

Rory wants to know who she is again, but she can’t rely on Jess to set her straight this time. She misses the self-assured mindset he brought out in her, the idea that she can do anything if she works for it, and the knowledge that one setback isn’t the worst thing in the world. She let Logan turn her into the girl _ he _wanted, a girl who was easy to date, a girl who was satisfied with a 200 grand dollar purse and a fancy apartment where she could live rent free. Dean turned her into a mistress, and Logan made her an odd high-society version of herself -- and while both of those relationships had their good along with the bad, she realizes that the girl that she knew was lost along the way, caught in the barbs and wires that came along with the men she loved. 

Most of the time, Rory doesn’t recognize herself anymore, and reading Tolstoy isn’t enough to make her reflection what it used to be. Everyone she’s loved has taken more than she thought she had given them, and she’d just let them. Rory thought she was just growing up, but now, she’s not so sure. Because she’s not anything like she used to be, the girl who had dreams higher than the clouds and worked so hard to get anywhere close to them. The girl who messed up, sure, but she didn’t let it derail her completely -- the girl who would pick herself up, brush herself off, and find her way back, always. Growing up doesn’t change you completely. You’re supposed to be yourself but different, better, wiser and weathered but all the better for it. 

And this baby -- this baby is a wake-up call. It’s not what she planned for, not what she wanted, but it’s what she _ has, _and that’s the grueling reality. Life does that to you sometimes -- it throws you off, and it’s up to you to create a new path, to find your way home once more.

This baby is not what she asked for, not the repercussions of an affair that she imagined she could handle. She thought her and Logan’s what-happens-in-Vegas-stays-in-Vegas-mindset was fine, but it wasn't right, wasn’t okay, and it’s going to hurt Odette eventually even if it didn’t hurt Paul. And it could’ve -- but even that would’ve been preferable to this. Because if Rory’s being honest -- really, truly honest -- she’d take everything back if she could just be herself again. She’d erase this baby, the book, the affair, Logan, her articles, everything, if she could just go back and be good again. And that’s the most heartbreaking thing -- being willing to give everything up just so she can build upon one good memory she’s been able to hold onto. 

Rory loves Logan, and a part of her always will -- but it’s a part of her that she doesn’t want, a part of her that leads her to sleep with married men or engaged men and break her own heart in the process. She doesn’t want to believe that that’s her, that she’s really that type of person. It’s a thought too much to handle, too scary, too shameful. 

She loves Logan, but it's not enough. Her love has _ never _been enough, it feels like, not when it counts. Dean left her three times, because she was never enough or she was too much or he doubted she was there at all. Logan cheated on her just because she was angry at him, thought he could do whatever the hell he wanted, and he could, because she let

him. And Jess. Jess is gone, again. He left without saying goodbye, again but -- but she loves Jess, too. She loves him, loves him so much it hurts. She’s realizing this too late, when he’s too far gone, and so is she. She’s lost him before she even had him, which is a knife to the heart. 

It takes a moment before Rory notices the tears that are streaming down her face. She tries to stifle a sob, but it’s no use. She starts to cry -- no, she _ lets _ herself cry, finally letting herself grieve for the girl that she’s lost. The girl that used to be hers, but is gone now, and she doesn’t know if she can ever get her back.

She grieves her relationship with Jess, which is definitely dead now. It’s possible he’ll never want to see her again, and she doesn’t blame him, she really doesn’t, because a part of her doesn’t want to see herself, either. She hates where she’s ended up -- alone, heartbroken, and breaking others, too. Being alone. That’s the scariest thing. 

She grieves what she’s lost, what her child has lost -- every dream that she realized too late. 

How can Jess still love her? How can he be so in love that he can’t fall for anyone else? How can he still love a girl who doesn’t exist? And how can that girl still love him?

After a while, she sobers up, wipes her eyes and clears her throat. Crying isn’t going to fix anything, even if she feels a little bit better. She needs to fix things, fix herself -- and it’ll be a tough road, full of brand new obstacles that threaten to stray her from the path for good. 

She’s terrified, no question about that. Rory wants to be a good mother, like her mom was, to raise a good kid and a happy kid no matter the circumstances. She wants that more than anything right now. 

She may miss Jess, too, and miss Logan -- she wants to be in love, like she always did, wants to be loved, the way she has been before. But until she fixes herself, she can’t mend her heart or raise another one fully intact. 

**Notes for the Chapter:**

> we out here fixing what asp broke


	16. Writer In The Dark

**Summary for the Chapter:**

> Rory finds Logan at her door with a surprising proposition.

**Notes for the Chapter:**

> I assure you I am in no way shape or form a Logan apologist but I have to acknowledge his privileged ass at some point so might as well be now  
This chapter ended up being a lot longer than expected honestly so enjoy!!!!

Logan doesn’t understand why this is happening to _ him. _Look, he knows he hasn’t always been a great person, and he’s made his fair share of mistakes, but perfection is overrated, anyway. People mess up. They should still be forgiven.

That’s why he’s so frustrated. Rory’s secret and ultimatum threw him for a loop, one he is still riding out, and he can’t fathom why _ this _ had to happen -- _ this _ being, of course, a baby that is not his fiancé’ s but sure as hell is his. It all feels like the opposite of forgiveness. Odette has definitely noticed his change in disposition, but Logan refuses to answer her questions every time. He knows she’ll find out eventually, from him or from (god forbid) someone else, but he wants to put it off for as long as possible. He _ needs _ to -- the arrangement between the two will only fall apart, and he doesn’t want that one bit. Logan doesn’t enjoy hurting people, contrary to popular belief. He wants to avoid this hurt for as long as he can.

Whose hurt is he really avoiding, though? Is it really about Odette, or is it about him? Because somewhere, deep down, Logan _ knows _ he’s being selfish. He can tell himself he’s keeping this secret for Odette’s sake all he wants, but at the end of the day, he just doesn’t want to face his mistake. Because that’s what this is, a mistake -- a baby that wasn’t planned and that he doesn’t want. He should be grateful that Rory gave him an out, and part of him is a little relieved -- but the guilt for feeling such a way plagues him day and night. It’s not that Logan doubts Rory’s capability to raise a child -- he learned not to doubt her ages ago -- but it is _ his _ kid, and he wants his kid to have a good life, a comfortable life, one where there’s plenty of opportunities and no unnecessary obstacles. Even though he had all of that growing up, ultimately, Logan was forced to be someone he didn’t want to be and to follow a path he didn’t want to follow. Even if he’s successful now, it wasn’t enough for him then, and he often wonders what would be different if he’d fought for what he wanted from the start instead of his constant complicity. There’s simply something about giving a child all the opportunities he had but with no terms and conditions accompanying them that’s just so damn appealing. 

It’s been almost a month that he’s been sitting on this secret -- this earth altering, world shattering, life changing secret. Logan _ knows _ he has to tell Odette. He’s waited too long for there to be any chance of a smooth resolution -- it’s a rough road from here on out. But even then, telling Odette is the _ right _ thing to do -- even if that fact only serves to make him bitter. 

Logan doesn’t want to be a father like this, and if he’s being honest, he never really wanted to be one in the first place, either. Sure, if it happened someday, at the right time and the right place, he wouldn’t protest. But this? This is all happening completely and entirely _ wrong. _

Now, he has no choice but to close his eyes, jump, and hope to god that he lands on his feet. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

It’s been nearly a month since Jess left. 

Christmas went by pleasantly -- Stars Hollow looked like a fairy tale, thanks to Kirk’s new fairy light business, and Rory couldn’t be happier celebrating with her mom and Luke -- their first Christmas as a married couple goes without a hitch. Even Liz, TJ, and Doula come over during Christmas day to gab and exchange gifts. It’s _ nearly _ perfect. The only thing that could make it better is if Jess was there.

Although Rory has been getting by fine without him -- she’s written a lot, read a lot, caught up on sleep -- her mind is plagued by thoughts of Jess more than she can put up with completely. She wants nothing more than to see him again, apologize, tell him how much she regrets what she’d said and how much she loves him, too. But this isn’t a Jane Austen novel, and she’s waited a little too long for any conversation on the subject to be amicable. 

Even though it’s been a little under four weeks since her revelation, Rory still hasn’t told her mother. Everything between them has finally reached a balance, one where Jess isn’t brought up and Rory doesn’t break down. And while she definitely feels guilty keeping this life altering secret from her mother, the only person she feels she can tell everything to, Rory wants nothing less than to upset this newfound equilibrium. Things are only now feeling right, finally feeling like they used to, if not for the fact that Rory is pregnant. Despite that fact, she is slowly but surely finding herself again, and that’s the most important thing. Telling her mother about her feelings for Jess can wait. It’s been a long road, and Rory’s still got miles ahead of her, but somehow -- somehow, she’s not dreading it at all. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

It’s the morning after Christmas, and Rory sits at the kitchen table with an Agatha Christie novel open on her lap. It’s impressive how many books she’s knocked out over the course of the last few weeks -- one Brontë, a Wells, and a Gaskell to name a few -- but she’s on a roll, and the feeling she gets when she finishes a book is the same as it was when she was young. 

Lorelai traipses into the kitchen with a loud groan, only slightly distracting Rory from her book. “Hungover?” She asks, not looking up.

“You wish you could relate,” Lorelai says bitterly, opening the fridge. “Gilmore the third may be an incentive to keep you from chugging an entire bottle of Founders’ Day Punch at once, but after a few more months, you’re going to--“

“Just drink your coffee,” Rory quips. “I’m trying to finish this book today, and I won’t get anywhere if you keep lamenting about the side effects of drinking five cups of Founders’ Day Punch.”

Lorelai crosses her arms defensively. “It was only four.”

“That counts as talking about it,” Rory reminds her in a scolding tone. 

“Geez, someone’s grouchy.”

“I’m not grouchy,” Rory argues. “I just want to read.”

Lorelai can’t help but smile. “It’s good to see you reading again,” she says softly. “I’ve missed it.”

Rory smiles in return. “I have, too.” She admits. 

They’re quiet for a moment before Lorelai speaks again. “So, have you been thinking up ideas for the snowman building contest?” She asks, putting some pop-tarts in the toaster for her breakfast. 

Rory scrunches up her nose in confusion. “Why is every town event delayed this year? The contest is usually way earlier in December.”

“This time? Taylor decided we didn’t have enough snow,” Lorelai replies. “But don’t you worry. The Firelight Festival isn’t going to be delayed, at least.”

“It better not,” Rory cautioned. “God, it’s been _ years _ since I’ve been able to make it to the Firelight Festival.”

The toaster dings, signaling that Lorelai’s pop-tarts are ready. “Oh, yeah, what’s it been? Five years? We’ve missed having you there,” Lorelai says, taking a bite out of one of the pop-tarts. 

“I’ll be there this year,” Rory promises. “Is Kirk still in charge?” The memory of Kirk’s frantic manner when preparing for the festival elicits a chuckle from her. 

“You’d have to pry that walkie-talkie from his cold, dead hands,” Lorelai concurs. 

Rory laughs. “Probably.” They both go quiet for a moment, but her mother breaks the silence again, with something very unexpected on Rory’s part. 

“Have you, uh…” Lorelai glances away awkwardly, knowing that this question will set something off in Rory, whatever it might be. “Have you heard from Jess at all lately?”

Rory’s eyes widen at the question. She and her mother had avoided any mention of Jess whatsoever since he left the night of the dance marathon, and she’d expected it to stay that way for a while longer. “No,” she says quietly. “I haven’t.”

There’s a beat of silence as Lorelai gathers her thoughts. “I’m sure you will soon enough,” She says soothingly. “And if you don’t, why don’t you give him a call?”

Rory rubs her arm absentmindedly. “I don’t know. He probably doesn’t want to talk to me, not after I…” She trails off in shame, unable to recount their last encounter. 

Lorelai shrugs. “Can’t hurt to try.”

“Is it fair of me?” Rory asks weakly. “Is it fair to try to start talking to him again after I hurt him? Again?”

Lorelai smiles bittersweetly. “Just give him a call and you’ll find out.”

Rory stares down at her lap. “It’s too soon to _ call.” _

“Then send a text,” Lorelai suggests.

“I don’t know…”

“An email.”

Rory groans. “Mom.”

“A letter. Snail mail’s underrated these days.”

_ “Mom.” _

“A smoke signal.”

It’s starting to feel too familiar. “Okay, that’s enough.”

“A nice fruit basket.”

“Mom,” Rory says firmly, “I’m just not ready.”

Lorelai bites her lip. “I hope you will be someday, kid. I don’t want you to lose his friendship because both of you were too scared to call.”

“I probably already lost it,” Rory says glumly. “After everything...all these years that he’s loved me and I just kept hurting him and hurting him and hurting him...I wouldn’t blame him if he just wanted to leave me behind him.”

“He doesn’t want that,” Lorelai insists. “Trust me.”

Rory frowns. “How can you be so sure?”

“Just am. Believe me, okay? He doesn’t want to lose you, either. So one of you is going to have to take the first step. Otherwise…” Lorelai shakes her head. “You’re going to never be able to stop thinking about what might’ve been.”

_ Too late for that, _ Rory thinks to herself bitterly. _ That’s all I’ve been able to do for well too long. _

-::--::--::--::--::--::--::--::--::--::--::--::--::-

“How much sleep have you gotten this week?” Matthew asks, concerned. “You look like you’ve stayed up five nights straight binge-watching _ Buffy _ reruns with an old stoner roommate from college.”

“Oddly specific,” Chris notes. “Could this possibly be drawn from real-life experiences?”

“Shut up.”

Jess, whom the question was directed at, chuckles. “Inspiration strikes when it strikes,” he says simply. “And when it does, I write.”

Matthew salutes him. “A true artist.”

Jess shakes his head in amusement. “Staying up all night got me twenty pages done, alright? That’s a good thing.”

“And it’ll give you a screwed up sleeping schedule and a headache to boot,” Chris laughs. 

Jess snorts. “I’m way ahead of you.”

“At least have some more coffee,” Chris insists. “I don’t want you crashing during drinks tonight, okay? We can’t have a repeat of the Matthew incident of 2012.”

“Hey,” Matthew objects from the couch. “I told you, I tripped.”

Jess raises an eyebrow. “And knocked yourself out?” 

Matthew simply flips him off, eliciting a laugh from Jess. 

Despite the heartbreak, these past few weeks haven’t been all that bad. Turns out emotional distress benefits Jess as a writer, so who is he to complain? His friends have been supportive and understanding and generally pleasant to be around, as per usual, so Jess really can’t complain.  
He still finds himself wondering every now and then about Rory. If she’s doing okay, how her pregnancy is going, or what she did for the holidays. He considers emailing her or maybe calling her, but he decides against it every time. It’s not that he doesn’t _ want _ to, because he really does, but she sent him away. Jess can take a message. She doesn’t want him -- not with her, not in Stars Hollow, and now? He doesn’t expect her to even want him in her life anymore. 

Even then, Jess finds himself feeling...okay. He’s doing well with work, he’s spending time with his friends, and he’s slowly working towards moving on. At least, he hopes -- as long as Rory holds onto the title of the only woman he’s ever loved, he’s not going to get anywhere. He just doesn’t know where to begin. 

He did go out on a date, a couple weeks after he got home, but it didn’t go anywhere. He couldn’t even get himself to agree to go to her apartment, let alone a second date. They parted ways amicably, a friendly face he can say hi to if he ever sees her again, but nothing more. Jess hopes that one day he can be happy with someone -- but god, the only someone he wants to be with is Rory. And he has a gut feeling that no matter how hard he tries, that might always be the case. 

“Jess. Hey, Jess!” He snaps out of his reverie when Chris shouts his name, finally grabbing his attention. “We asked you what you thought about Daniel’s manuscript!”

“Oh. Oh, right,” Jess says, blinking a few times to reorient himself and remember who they're talking about. “Daniel.”

“Yeah, that guy we met with yesterday who proposed a--“

“--novel about a misunderstood film major,” Jess suddenly says, remembering. “Oh, God, it was terrible.”

“That’s what I said!” Matthew exclaims, looking pointedly at Chris. 

Chris groans. “Fine. We can turn him down. But then we sign on that girl Zoey.”

“Her idea wasn’t any better,” Jess points out. “She’s trying to make it big with some epic love story, but there are literally no more variations of _ Pride and Prejudice _to tell.”

“Isn’t that essentially what you’re writing?” Chris says, regretting it as soon as he asks, but Jess simply shrugs. 

“It’s different.”

“How so?”

Jess frowns for a moment. “I can’t speak for Zoey,” he begins slowly, “but whatever I’ve been doing that’s been keeping me up all night is from the heart. Something that happened to me. I’m not trying to make something up that never happened just so people will put me on a pedestal and praise me as the next Jane Austen.”

“Then why not try to give yours a happy ending?”

Jess stares at Matthew in surprise. “What?”

“Like, okay,” Matthew explains, “sure, your love story is tragic and all that, right? But you’re letting it end like that, Jess. Where’s your ‘holding a boombox outside her window’ moment? Why aren’t you trying to give it a good ending?”

“‘How little of permanent happiness could belong to a couple who were only brought together because their passions were stronger than their virtue,’” Jess recites in response. 

Matthew stares at him, puzzled. “What?”

“Pride and Prejudice,” Chris explains.”You could’ve guessed that from context.”

Matthew shakes his head. “Don’t you start quoting Jane Austen at me just to throw me off my rhythm.”

“It’s your fault if you’ve never read it,” Jess argues. “Look, Rory and I weren’t made to last. We went too fast too quick without talking about anything that actually mattered.”

“Trying again doesn't mean you repeat the same mistakes.”

Jess lets out a deep and long sigh. “I have to put this in the past,” he says, almost begging, but it’s just the same ineffective thing he’s been telling himself for years. 

“You keep saying that, but how much are you actually doing to make that happen?” Matthew points out. “You can’t even sleep with another girl right now, or even go on a second date. You’re obviously stuck on Rory, and maybe you always will be, but it’s not a lost cause.”

Jess gives his friend a smile. “Matthew, I appreciate this, I do, but I’m okay. I’m happy. I’ve been happy for the past ten years.”

“But--“

“God, if all my readers end up as passionate about my relationship with Rory as you are, I’m a little scared to see what’ll happen,” Jess quips with a chuckle. 

Chris laughs, but Matthew remains unconvinced. “You’re not as happy as you could be, Jess.”

Jess raises an eyebrow. “Since when are you so pro-Rory? Last I checked, you _ hated _ her and exclusively referred to her as ‘the ex.’”

“Don’t think of this as a pro-Rory speech,” Matthew says. “It’s more of a ‘if she’s what makes you happy then I want that for you’ type of thing.”

“Don’t get all mushy on me, Matthew.”

Matthew remains unfazed. “I just think you might regret it if you don’t try.”

Jess exhales slowly. It would be easy to just shut Matthew down and write this off, but for some reason, it’s appealing. The romantic in Jess that won’t quite die wants him to follow Matthew’s advice. But the rest of him? “You know I’ve always been more of a tragic love story kind of guy,” Jess argues weakly.

Matthew holds his firm gaze. “Doesn’t mean you have to live one.”

“Let me get this straight,” Jess says. “You, who begged me to come home for a solid month, want me to go _ back _to Stars Hollow to try to win back the girl you’ve hated for the last ten years?”

“People change.”

Jess looks over at Chris for help. “Chris?”

His friend shrugs. “Matthew might have a point for once.”

Matthew shoots Chris a glare, but moves past it. “I don’t know. I just think it might be good for you is all.”

“No.”

“Jess.”

“No!”

_ “Jess.” _

“Fine! I’ll go for _ one day,” _ Jess concedes, “just to get you off my back.” When he sees Matthew’s triumphant smile, he continues, adding, “And no promises I’ll try to be with her again. Mending our friendship is enough for me.”

Matthew mutters something about _ self sacrificing idiot _ and _ what does it take to make him help himself?, _but the conversation tapers off. Jess resolves he’ll drive to Stars Hollow the next day, say hi to Luke, say hi to Liz and TJ and Doula, and then see Rory. Maybe. If the timing is right, and nothing else is going on, maybe. But he’s not making anyone any promises, especially himself. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

It’s only a few days until New Years, and Rory is _ nearly _ done with her first draft of her book. She’s been making some real headway over the past month, writing almost nonstop, and she’s so close to being done. She’s sitting on the couch and working when she hears a knock at her door. It’s strange -- both Luke and Lorelai have their keys, and she’s not expecting anyone -- but she stands up anyway and goes to answer the door.

She doesn’t expect to find Logan on the other side.

He’s disheveled -- he probably came here straight from the airport, Rory thinks, noting his bag, wrinkled shirt, and messy hair. Once upon a time she might’ve found this look attractive, but right now, she’s only in shock. “Logan?” She says pointlessly, but she can’t think of anything else to say.

“I told Odette,” he says suddenly. 

Rory blinks a few times in surprise. “Oh.”

“I told Odette. She’s...she’s mad. So I…”

“So you ran,” Rory deadpans. Logan, a little agitated, doesn’t reply. “Are you...are you guys done?” She cringes at the hint of hope she hears in her voice when she asks. 

Logan looks away guiltily. “No. Not...not yet.”

“What are you doing here, Logan?”

Logan pauses before he replies, and when he does, he sounds desperate -- a sound that nearly breaks Rory all over again. “I can’t do this without you,” he says pleadingly. “And you can’t do this without me, either. C’mon, Rory, this is _ our _ kid. Shouldn’t it be given everything we can give?”

Rory closes her eyes and swallows. At any other point, she might’ve been glad to hear Logan say this or anything like it. But after ending their affair only a couple months prior, and how he’d reacted when she’d first told him she was pregnant, it leaves a bad taste in her mouth. “Logan--”

“You know I’m right,” Logan says, this moment reminding Rory all too much of one with another boy years ago. “You and me, Rory, we can raise this kid together -- isn’t that what you want?”

Rory blinks back the tears that are threatening to spill. “Why all of this _ now?” _ She chokes out. “Why not when I first told you a month ago?”

Logan opens his mouth to answer, but then closes it, and opens it again, but no sound comes out. Then, Rory knows she has her answer.

“I don’t want this if it’s just because Odette might leave you,” she declares. “I only want this if this is really what you want. But I...I don’t think that it is.”

Logan’s brow furrows. “It doesn’t matter why. It just matters that I’m here.”

“I wish that was true,” Rory murmurs. “But it’s just...it’s not.”

“So, what?” Logan demands. “So you’re just...saying no? You’re going to do this on your own?”

Rory bites her lip. “I’m not alone, Logan,” she says. “I’ve got this whole town that always helps me get back up when I fall. And you...you have a _ fianc _ _ é. _ Go back to her.”

Logan blinks multiple times in confusion. “I can’t be without you.”

Rory sighs. “We’ve been through this before, Logan.”

“Rory, I lo--”

“Don’t,” Rory says quietly. “Please, just...don’t.” 

Logan stares at her, confused. 

“Part of me is always going to love you, Logan,” she murmurs. “But...but it needs to be over now. We’re not in the same place anymore. And maybe...maybe we were never made to last.” As hard as it is for her to say, Rory knows she’s right. As much as she loved Logan then and no matter how much she loves him now, the connection they had isn’t enough to hold them together. She’s learned a lot by re-examining their relationship over the past month, and she knows now that they just weren’t compatible enough to make it stick. It was good when it was there, but now it’s gone, and they’d been foolish to try to bring it back. 

Logan takes a moment, but then he seems to understand. And while it stings, Rory is also relieved -- she doesn’t want to fight him on this. It only makes it harder to let go. 

“It was good, though, wasn’t it?” He murmurs. 

Rory can’t help but smile softly. “Yeah. It was.”

Logan gives her a nod. “Goodbye, Rory,” he says, his voice kind. And then, he turns and leaves.

Rory stands at the door for a little while longer, puzzled by the odd sense of relief she feels as he walks away, so different than how she felt when it was Jess. She never imagined having this sense of closure, but now that she does, it feels good. And while she loves him -- and she has a feeling that the attachment she has to him will never truly fade -- Rory wants to be able to remember when it was good. Because while there were times when loving Logan was hard, she doesn’t want the good times to be poisoned by a final and unfortunate parting of ways. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

The “Welcome to Stars Hollow” sign is anything but welcoming this time around.

Driving back to Stars Hollow doesn’t do much other than force Jess to remember the past. It’s almost as if there’s a “previously on” playing in his mind, reminding Jess of every what-if and might’ve-been. But it’s worse than the last time, because now he's entering enemy territory, just like he was ages ago. He’s disappeared again, and surely the rest of the town will have resorted back to how they used to feel about him.

But he doesn’t get a chance to find out. 

The first person he sees when he gets out of the car isn’t a townsperson, but someone he hasn’t seen in ten years -- and hasn’t wanted to, either. Logan blinks in surprise at the sight of Jess getting out of his car. Neither speak, but neither of them move -- it’s some sort of stalemate; either they won’t move, or they _ can’t _ move. Upon seeing Logan, Jess is instantly filled with a sense of dread and loathing, and he assumes Logan feels the same, based on the look on his face. 

Logan is the one to break the silence. “Jess.”

Jess raises his eyebrows. “Well, of all the gin joints in the world.”

Logan assumes that pompous smile that Jess loathes, taking his car keys out of his pocket and fiddling with them so Jess can see the Porsche logo. _ Figures. _ “What brings you here?”

“I have family here,” Jess says cooly, “which is more than I can say for you.” He moves to walk past him, but Logan sidesteps to block him. “You’re not going to ask me what I’m doing here?”

“Didn’t think you would tell me,” Jess says dryly, “so I figured I’d skip the pleasantries.”

“Oh, I wouldn’t. But I’d appreciate the gesture.” 

Jess gives him a wry smile. “Right. Now, if you don’t mind…”

Instead of letting Jess pass, Logan rests his hand on the hood of Jess’ car, and Jess knows it’s a lost cause to try to avoid this. He doesn’t understand how after all these years Logan can still have this superiority complex -- he thought for sure someone would have knocked him down by now. Logan doesn’t even have anyone to be territorial about anymore, anyway; not when it comes to Rory. 

“So, what have you been up to, Jess? What is the golden author up to these days?” Logan asks, innocently enough, but Jess catches the condescending undertone. 

“This and--“ He catches himself before they can repeat the past any further. “Nothing that would interest you.”

“How can you be so sure about that?” Logan raises his eyebrows. 

Jess exhales slowly to calm himself to make sure he doesn’t punch Logan in the face. He’s above and beyond living on a whim, acting on his anger like that, but something about this asshole makes him want to forget all of that, if just for a moment. “I haven’t lined anything in gold lately, so I don’t think it caters to your select audience.”

“Ooh, what’s with the attitude?” Logan replies dramatically. “We’re just getting along, catching up, learning the _ this _ and the _ that.” _

Jess purses his lips, one moment away from snapping. “Don’t push it, Huntzberger.”

“Don’t pretend you’re on a higher level than the rest of us, Jess,” Logan says. “What says you can’t talk to an old pal?”

Jess snorts. “Oh, please. You’re one to talk.”

“Let’s stay friendly, now.”

“Friendly?” Jess asks through gritted teeth. “I don’t know if I’m up for playing nice today.” 

Logan’s expression doesn’t give away anything, but the all too memorable patronizing tone to his voice increases. “You’re not writing anymore, then? That’s a shame. I was just about to put in an order for a few copies of your little pocketbook, make sure you don’t fall off the face of the earth.”

“Don’t worry about me. I pulled a Dorian Gray, so I think I’m set.” Jess would be lying if he said he didn’t take any pleasure in the lack of understanding on Logan’s face. “I like where I am. I’m not looking to make the big bucks.”

“Clearly,” Logan mutters, eyeing Jess’ Jeep Grand Wagoneer. 

With every passing moment, Jess is less and less sure he can keep his composure. Every comment Logan makes is dripping with a sense of superiority that is severely misplaced. Jess could tear him down in seconds, and it’s tempting -- his knowledge about Logan cheating on Rory and the affair are just waiting to be used against him, bring him down to the level he belongs on. “I actually had somewhere to be, so if you don’t mind…” 

Logan smiles, but there’s no kindness in it. “Go ahead,” he says, gesturing towards Jess’ car door. “Don’t let me hold you up.”

Jess locks his car with his keys. “Not what I had in mind.”

“This is sad, Jess,” Logan says. “You should go. I don’t think trying to win back your high school sweetheart is a good idea for the day. You two are in the _ past, _ aren’t you?”

Jess presses his lips together, holding onto whatever control he has left. He hates that Logan is right -- and whether Logan can actually tell or he’s just trying to rile Jess up, it still feels underhanded. Jess could let slip what he knows right now -- but the reminder of Rory holds him back. Instead, he calms himself, keeping his expression fairly emotionless as he looks at Logan. “I have been reading a lot,” he begins, a light tone to his voice, “and I think it’s a hobby you should pick up. I can lend you the book I’m reading,” Jess says, pulling out his copy of _ Far From the Madding Crowd _ out of his back pocket, “but you might want to start with something at your level. May I recommend _ Alexander and the Terrible, Horrible, No Good, Very Bad--” _

“--maybe we can see each other again when you’re in a better mood,” Logan sneers, cutting Jess off. He opens his car with his keys, and before he gets in, says, “But I’m not paying for your meal next time.”

After Logan drives off, Jess angrily kicks at some rocks by his feet. He cannot stand the rich and pompous, the high and mighty, anyone like Logan -- and the smug look that Logan has no right in having, but does anyway, makes Jess furious. 

Encountering Logan has drained Jess of any motivation he had to go see Rory, or anyone else in this town. He unlocks his car and climbs back in, slamming the door shut with all the force that he can. Turning the key and driving away, he’s only able to think about how _ stupid _ this is -- and how foolish he was for thinking he could change it. 

**Notes for the Chapter:**

> jess nation how we feelin


	17. Can't We Be Friends?

**Summary for the Chapter:**

> Rory reaches out to Jess for the first time in a month.

**Notes for the Chapter:**

> These emails are actually really fun to write so bear with me this is pretty self indulgent  
Also: I know the timeline of this is a little fucked just go with it

Rory stares at her computer, tapping her fingers against the table as she ponders her choices. She eyes the clock at the top right corner of her laptop -- it’s only five minutes to midnight, and Rory has a decision to make. Does she want to start off her new year with a thousand words unsaid, or does she want to try to win her friend back? Her cursor hovers over the _ send _ button, but then she retracts her hand, unable to decide. She knows it’s potentially stupid, and there’s a strong possibility he’ll ignore her email altogether, but she has a feeling she might regret not sending it. Even if she worries that there’s a small chance of getting her friend back, there’s an even smaller chance if she does nothing at all. So, taking a deep breath, she throws all caution to the wind and hits send before she can stop herself. 

There’s no turning back now.

-::--::--::--::--::--::--::--::--::--::--::--::--::-

It’s New Year’s Eve at Truncheon, which means that Matthew has the ball drop on the TV and Chris is struggling to open a bottle of champagne while Jess has a book open on his lap. In their early to mid twenties, the three would go to bars, and Jess would watch his friends attempt (and mostly fail) to find girls to kiss at midnight. Nowadays, they sit around either downstairs, upstairs in the apartment, or at Jess’, with the television on and at least one comment from Matthew on “How sad are we?” Tonight is no exception. 

There’s a _ pop _ and a cheer from Chris, who exclaims, “Who wants a glass?” Jess raises his hand in acknowledgement, and a moment later he has a glass of champagne in it. He takes a sip, and the moment he swallows, there’s a _ ding _ from his computer. Furrowing his brow, Jess leans forward to read the notification on his laptop -- an email. From Rory.

Intrigued, Jess brings the laptop from the coffee table in front of him to his lap, moving his copy of _ House of Spirits _ to the side. Opening the mail application, he sees that he has in fact received an email from Rory. “What’s that about?” Matthew asks, noticing Jess’ change in expression from content to something resembling confusion. 

“Nothing,” Jess says. Matthew shrugs and takes Jess at his word for once, but Jess doesn’t shrug it all off as easily. He stares at the email, his cursor hovering over it. He considers sending it to the trash without reading it, but before he can, he takes the plunge and opens it. It’s five minutes to midnight, almost the new year, and Jess is curious to see what Rory has to say to him. It’s been a month of radio silence on both of their parts, so something must have prompted this sudden attempt at communication. He wants to know what it was. Besides, if he doesn’t want to reply, he doesn’t have to in the slightest. He opens the email and starts to read it, hating how his heart twinges the moment he begins. 

From: Rory Gilmore (rorylgilmore@gmail.com)

To: Jess Mariano (jmariano@gmail.com)

Subject: New Year, New Plan

He chuckles softly and somewhat involuntarily at the subject she’s written. Matthew glances over at him briefly, but Jess pays him no mind. He reads on.

Dear Jess,

Part of me thinks this is a mistake, emailing you in the middle of the night after no word for a month, but, hey. It’s a new year (almost) and there’s always a chance you won’t even read this, so I don’t think there’s any harm in it. At least, I hope not. I also really hope that you won’t ignore this, because I really do have a lot to say to you, but if you decide not to read this, I won’t blame you. I’ve done and said some shitty things to you, so I totally understand if you’re angry or if you hate me. Consequences are what they are, and this is all I can do to extend an olive branch, so to speak. You can throw it back if you want. I’ve moved on from the self pity thing, and I have to tell you, it’s done wonders for my figure. 

In all seriousness, though, I owe you an apology. First off, I’m sorry for what happened the last time I saw you. I won’t recount what happened, because we both remember, unless you’ve gone and gotten yourself a lobotomy, and in that case, this whole email would be pointless, wouldn’t it? I wish it could have gone down differently, but I guess it was a lot at once, and I just didn’t know what to do or what to say. It’s no excuse for turning you away like that, I know, but it’s just what happened, and I can’t change that, no matter how much I want to. I really am sorry for hurting you again. It’s a bad habit and I don’t mean to do it, but somehow I still do, and I really hope you can forgive me. 

I’m also sorry for just...everything. That’s a really broad term, but there are so many things I regret, and listing them all would be wasting a lot of time. I hope one day we can sit down and really air it all out, say everything we need to and work it out, but for now, this has to do. I wish I hadn’t lashed out at you when I saw what you had been writing. There’s a lot of unresolved things between us, and I think it surprised me and everything just came to the surface. Eighteen year old Rory bottled up a lot of resentment, and I never let her examine it. That fight is on me for that reason and probably more, but like I said, I’m trying to stop feeling bad for myself. I take responsibility but I won’t spend any more paragraphs lamenting over it.

Whew! I’ve talked a lot about us and my feelings so far so I think I’ll cover some other topics, too, so it’s not too much. Stars Hollow is the same as always, except that one of the ceramic unicorn stores closed down. The whole town has been upset about it all week, but the owner retired and no one has stepped up to take over. I already did that with the Gazette, so don’t expect to see me behind the counter of _ Joe’s Little Unicorn Emporium _ with a pastel pink apron anytime soon. 

The town misses you, too, believe it or not. Miss Patty seems especially bummed, but I really don’t want to dwell on why, so I’ll leave it on that. Taylor is the only one who has shown any positive emotion about it, but it’s Taylor, so I wouldn’t take it personally. He still thinks you’re seventeen, so it says more about him than it does you. I think Luke is sad that you didn’t say goodbye, but you know Luke, he hasn’t said anything about it. But I think he liked having you around again. I know I did. 

In other news, what more can I say? Doula is good, but you’re probably in touch with her, anyway. I saw her and Liz at Doose’s the other day, and all is well. I’m a little worried about the amount of cabbages they bought, but I’ve learned not to ask the Danes family any questions. I’m sure the answer will be more bizarre than I care to hear. Andrew has also suddenly stocked at least five copies of _ The Subsect _ for some reason, so I bet the entire town will be clamoring for more Jess Mariano works in no time. I’d love to say I had some part in this, but I actually didn’t. Not too surprising, though. It was only a matter of time before they recognized you for who you are, which is an amazing author.

Logan came by the other day. I know you hate him, but I felt like it was important to tell you. Nothing happened; I sent him away. But basically, he told Odette (his fiancée) about the whole situation, and she’s understandably not too happy about it. Everything is kind of a mess, but at the same time, I’m figuring it all out. I’m excited about the baby, more than I was before. 

The pregnancy itself is going well! I keep having to fend off Paris, who has a lot of unsolicited advice, but I’m secretly grateful to have her so invested in it. (Don’t tell her I said that, though.) I’m only two months, so there’s a long way to go from here, but I’m not as scared as I used to be. Oh, it’s definitely terrifying -- but my mom has been amazing and I know this town won’t abandon me. Stars Hollow is wacky a lot of the time, but they’ve always been there for me. 

One more thing, which could arguably be one of the more important or interesting parts: the book is going really, really well! I’m almost done with my first draft, and I’m so happy with it. I’m a little scared it won’t be something people will want to read, but it means a lot to me, and it shows in the writing, so I think that might be worth something. I can’t take all the credit, though. I owe it all to you, Jess, I really do. I wouldn’t be doing this if you hadn’t suggested it, and if you don’t mind, you will definitely have a whole paragraph (or several) devoted to you in the acknowledgements. Thank you so much. I honestly don’t know what I would do without you. If it weren’t for you, I would never have gone back to Yale and probably _would_ be working at some ceramic unicorn store. Thankfully, that’s not the case! But I have had a lot of free time lately, so besides writing my book, I’ve been doing a lot of reading. It’s definitely helped me start finding myself again, and that I owe to you, too. 

So, what about you? How’s Truncheon? How are the guys? You mentioned last month that you guys were talking about expanding. Are you guys still talking about that? I know you like to keep it lowkey and out of the spotlight, but it’s still something to consider, right? You’ll make the right decision, I know it. 

I hope this isn’t inappropriate of me, this whole email, but I had to apologize and just tell you about everything going on. You’re important to me, Jess, and you always have been. I just hope it’s enough, because I really don’t want to lose your friendship. It really does mean everything to me.

Have a happy New Year, Jess. You once told me that you think that New Year’s is pointless, because there’s no real difference between December 31st and January 1st, but I disagree. I think a new year is a fresh slate, which is just what I need. I’m going to go watch the ball drop with my mom and Luke, so this is me signing off for now.

Your very sorry friend,  
Rory.

When Jess is done reading the email, he looks up, blinking a few times, combatting the sudden surge of _ relief _ that overcomes him. He had been so worried about her not forgiving _ him, _but after reading her email, it seems like that was never even an issue to begin with. She’s not angry with him at all, and for that he is unbelievably grateful. This isn’t like the last time she broke his heart -- even if he blamed himself for not asking if she was with anyone more clearly before he kissed her, she had led him on, and he couldn’t take responsibility for that, even if he would if he was able to. 

It’s one minute to midnight, so Jess closes his computer and watches the ball drop with his friends, temporarily putting off his response to her. He still doesn’t think New Year’s is anything special, like Rory speculated in her email, but he thinks that maybe, just maybe, a new leaf has been turned. This could be the first step in fixing everything with Rory. Above all, he wants her in his life, and she said she wants her _ friend _ back, and he’s okay with that. If she doesn’t say she has feelings for him like he does for her, then friends is good. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Rory checks her email obsessively for the next few days. She knows he’s busy with his job and his friends and the whole life he has without her, but she can’t help but be impatient. She wants to hear what he has to say, if he’ll forgive her, if they can be friends again. As much as she wants to be more than that, she knows that it isn’t right to expect more. If he moved on in the past month, which, honestly, she doubts he has, obviously, it’s a lost cause. And even if he hasn’t, even if he _ still _ loves her, _ she _ turned him away and can’t just ask for him back. Maybe, if things had been different, or if they’d made different choices all those years ago…

When she refreshes her email and sees his name at the top, her worries fly out of her head. She had begun to think he really had ignored her email, but she reprimands herself for it. That’s not something Jess would do. 

She begins to read eagerly.

From: Jess Mariano (jmariano@gmail.com)

To: Rory Gilmore (rorygilmore@gmail.com)

Subject: Re: New Year, New Plan

Dear Rory,

I’m sorry I didn’t reply sooner, but things at Truncheon have been insane when it comes to workload. I suppose I’m in the minority of people who think New Year’s is pointless, because it seems as if a lot of people have resolved to be an author in 2017. We have tons of manuscripts to read through, so it’s a miracle I was able to actually carve out time to write to you. Believe you me, as much as I love my job, I’d rather be writing to you than reading yet another manuscript by an F. Scott Fitzgerald wannabe. 

I’ve thought about what happened at the dance marathon all month, and it’s safe to say neither of us handled it very well. I want you to know that I don’t think there’s anything to forgive on my end. I was never angry about your reaction; under the circumstances, it was perfectly justified. But, if you need to hear it: I forgive you. _ That _ is a promise.

I didn’t enjoy leaving the way I did, and I’m sorry for it. I know you probably meant you wanted me to give you space, but I left anyway. I’m still learning not to do that.

I feel bad for not saying goodbye to Luke, too, but I’ve stayed in touch with him as always, so things are fine. He may miss having me around, but I agree that it’s not his thing to acknowledge that. Consider it a Danes family trait. My name may be Mariano, but I’m still a Danes man, so the trait may be inherited. I’ve heard my grandfather wasn’t the most talkative, either. 

Going back to what I was saying before: our past is indeed messy, and I agree that someday, we need to talk it over. I was never good at opening up back then, and while it’s still a struggle at times, we owe each other to be honest. Even if it didn’t end well that night, I’m glad you talked about what you had imagined for us back then. At least there’s still some good left to reflect on. 

I meant what I said that night, too. My feelings haven’t changed over the years, and what that says about me, I don’t know, but it’s just how it is. It’s okay if you don’t feel the same, but I just want to be honest. In another life, maybe things would be different, but they’re not. The most important thing is that I want you in my life, and if you want to be friends, I’m more than good with that. Whatever you want, all I ask is that you say it explicitly. I don’t want any more misunderstandings between us, okay? 

You’ve had a real impact on me, and I hope you know that. I wouldn’t be where I am or who I am without you, either, so you’re not alone in that department. You were the only person that really believed in me and encouraged me, and that pushed me to actually do something with my life. And as painful as it was then and to look back on now, I think that what happened between us was probably essential in shaping me. But, I realize now that dwelling on the past like that isn’t doing us any good. It’s all I did for years, and I can assure you it is not a productive pastime. 

In any case, I really am incredibly proud of you. I can’t wait to read your book -- I would prioritize it over all the manuscripts I have to read if I had the option. It comes from the most _ real _ side of you, and that’s what moves people. I don’t think attracting readers will be a problem. 

I’m glad your pregnancy is going well, too. I don’t have much to ask on that part, seeing as I know next to nothing about pregnancy or babies or anything, but just know that I remain extremely happy for you. Will you find out the sex beforehand or leave it a surprise? Either way, I’m betting on it being a girl. Gotta continue that Gilmore girls legacy, right? It’s early on, I know, but have you started thinking about names yet? Matthew recommends the name Matthew, unsurprisingly, but for the record, I didn’t ask him. (He likes to read over my shoulder, which probably won’t come as a surprise considering everything else I’ve told you about him.)

As for the Logan subject, I won’t put in my two cents, considering how I feel about the guy. All I’ll say on that is you have good judgement, and you’ll make the right choice when it comes to you and the baby. I hope for your sake everything ended well. 

Sometimes I wonder if Stars Hollow is some sort of social experiment, because if the town is _ that _ upset about one of the _ twelve _ ceramic unicorn stores shutting down, that raises a lot of concerns on my end. But besides that, tell Andrew I appreciate him putting _ The Subsect _ in stock. We’re printing some more at Truncheon soon, actually, as a way to spread the word about our press. I don’t expect it to do much, but it doesn’t hurt the budget, so what’s the harm? 

Truncheon is good, even if we’re drowning in work. I think we’ve put the expansion on the back burner for the time being, though. We need to talk it over in depth before any decisions are made, and there’s no time for that. Who would run the other office, where it would be, and all those questions need to be analyzed in depth. Money is also a concern; even though we like being small, and an expansion won’t necessarily transform us into the second HarperCollins, the budget can be tight at times. We work hard, but we all know hard work isn’t rewarded like it should be. I don’t want to be rich, in any case. I’m good where I am. Being ridiculously wealthy has never been an aspiration of mine. 

The guys are good for sure. I hope someday you can meet them properly, but on the other hand, they’re not the most mature. They’ve never met you, but they stick to their version of the “bro-code” religiously, and while it’s well intentioned, I don’t think they’d be the nicest to you. They won’t trust an ex until you prove yourself somehow, and I wouldn’t put it past them to piece together some ridiculous quest or task. I love my friends, but sometimes they’re a little too dramatic. 

You have to tell me about what you’ve been reading so I can check the books out or reread them so they’re fresh in my head for us to discuss. I wish I had more time to read, but like I said, I’ve been preoccupied. Most recently, I finished _ The Things They Carried _ by Tim O’Brien. I mean, the guy doesn’t really know how to write women, but it was interesting how he wrote about the Vietnam War and the impact it had on people like him. I’ve also been reading a lot of Brontë recently, and I have to say, they know what they’re doing, but I didn’t like _ Agnes Grey _ as much. Anne just isn’t my favorite. I also read _ The Love Letters of F. Scott and Zelda Fitzgerald, _ and while those two were a little messed up, it supplies some really lovely quotes for Chris to print out and frame. There’s just something about “I love her, and that’s the beginning and end of everything” that just makes you want to sit down and watch a Nicholas Sparks movie. Okay, so, maybe I’ve read more recently than I realized. I find the time, but my sleeping schedule suffers. 

I’m going to end this email before it gets too unruly, but I’ll definitely have more to say in response to your next. I just want to say again that it’s okay. Things don’t always work out the way we want or expect them to, and if we fight too hard to repeat the past, it only breaks us more. To quote the great F. Scott Fitzgerald: “So we beat on, boats against the current, borne back ceaselessly into the past.” 

From,

Jess.

There’s a lump in Rory’s throat as she finishes reading his email. She’s more than grateful to know that he doesn’t blame her, that he doesn’t hate her, and that he never was mad in the first place. But the rest of his words are weighted, dense and packed, carrying so much that she’s afraid he’ll break under the pressure.

Jess still loves her, and that’s what hurts. He isn’t shying away from it, and she appreciates his honesty, but it stings just as much. She just wishes she didn’t have to hurt him.

The timing just...isn’t right. If the circumstances were anything but this, Rory would get in a car and drive to Philadelphia and just kiss him until the rest of the world falls away. But Jess is right -- the circumstances are what they are. Believing anything but is foolish. There’s nothing they can do about it, nothing they can say to change the past, nothing to do but leave everything between them unsaid. The fact that it isn’t one-sided is what kills her -- she’s doing this to herself. But it’s the right thing to do. The hardest thing usually is. 

So, swallowing her feelings, she hits reply and begins to write. 

  


**Notes for the Chapter:**

> "in another life" just hits differently yanno


	18. Snowmen and Secrets

**Summary for the Chapter:**

> Rory and Jess continue to email. Rory tells Lorelai about her realization.

**Notes for the Chapter:**

> Sorry that this chapter is kind of lame. I promise the next one isn't!

From: Rory Gilmore (rorylgilmore@gmail.com)

To: Jess Mariano (jmariano@gmail.com)

Subject: Re: Re: New Year, New Plan

Dear Jess,

I can’t tell you how glad I was that you didn’t just delete my email without reading it. I know that that’s not a Jess move, and I don’t think I really believed you would, but we both know that fear isn’t always rational. Anyway, I really am so happy that you wrote back. I wrote my reply immediately after, but I’m waiting a day or two to send it so I don’t seem desperate. I guess telling you that kind of defeats the purpose, but oh well.

Thank you for being so understanding, Jess. I feel like I don’t deserve the amount of kindness that you’ve shown me, based on all the things I’ve done, to you and just in general. It’s hard to not get down on myself about that, but if you can forgive me, I think I can forgive myself. And yes, I do just want to be friends. I understand you needing me to say it outright -- a lot of problems can be avoided that way. Thank you, though, for being honest. It’s a small gesture, but you have no idea how much it means to me. I think it’s safe to say we’ll always be important to each other, and however that is, it’s good to be on the same page. 

But you're right, you’re absolutely right about us and the past and everything. I shouldn’t be surprised, though, seeing as that’s usually the case. I agree that trying to repeat the past is dangerous, but did you have to cite Fitzgerald?    
I know you’re going to ask what I have against Fitzgerald, so I’ll just explain now. God, I can  _ hear _ the incredulity in your voice. I get that the guy had a way with words, and there are a select few quotes that do sound really nice, but you have to admit, he tried way too hard to make his writing sound pretty, to the point where sometimes, his writing is incoherent!  _ The Great Gatsby _ is exhibit A. I realize this is an unpopular opinion, but I feel like too many people blindly praise it. There are tons of books that criticize the American dream, so I don’t see why his is special. If you want beautiful quotes and social commentary, Margaret Atwood has plenty of both. 

I agree with you about O’Brien, though. While there’s a case to be made about whether or not his lack of skill when it comes to writing women means he’s a bad author overall, he’s really effective when he writes about the war, so I can’t discredit him completely. I haven’t read  _ The Love Letters of F. Scott and Zelda Fitzgerald,  _ but you’re right about that quote. I can’t believe you didn’t like  _ Agnes Grey, _ though! I know Anne isn’t as acclaimed as her sisters, but she’s not a bad writer. 

You know I’m always up for telling you what I’m reading. I finished  _ And Then There Were None _ by Agatha Christie about a week ago, and let me tell you, I don’t know why I didn’t read her books earlier on. I never thought myself one for mystery novels, but she may be changing that! Other than that, I read  _ Fear and Loathing in Las Vegas, The Stranger,  _ and  _ Much Ado About Nothing. _ I also reread  _ Persuasion _ and I came across my copy of  _ Howl,  _ so of course I had to read that. I have to say, seeing all your notes in the margins was really nice after all this time. If you ever have more of your books you want to share, let me know -- I know you can’t help but write in all of them. 

I’m so glad that Truncheon is printing more copies of  _ The Subsect! _ I know you don’t think highly of your own work for some stupid reason, but you have to believe me when I say that it is  _ amazing. _ I need another Jess Mariano novel ASAP. It’s been too long without seeing your name in print like that, and I really want to fall in love with your characters again. You were meant to be an author, Jess. It really is the perfect thing for you, and whatever you write next, I’ll be first in line on release day. 

I really do love writing my book, but sometimes I wonder if being an author is the right thing for  _ me, _ you know? I don’t dislike it, but I’ve always felt like I was meant to do something else. I love reading and I always have, but I wanted to be a journalist for so long and I hate that I let myself down like that. I think that as great as the Obama campaign job was, it set me down a path that wouldn’t last. If I had gotten the job at the New York Times, or kept that other newspaper job, I would be somewhere completely different. While it was sustainable for a little, the freelance life isn’t for me. The unexpected is good in some cases, but not all -- job security is much more preferable, at least for me, and I should’ve known I wouldn’t be able to make this last. I know you said that there’s still time, but I can’t help but feel like it’s too late. I could always get my Master’s so I can teach at Chilton, but that doesn’t feel like something I’d be happy doing permanently. I wonder if Christiane Amanpour still has the same email. I could use some of her wisdom. 

Honestly, I just want to be back in the newsroom. The arguments, the sound of people typing, heated discussions and disagreements, Paris yelling...I miss it. It’s been so long, though, so many years since I was in one, had a job in one -- not just a visit or freelancing or a year as editor of a college paper, no matter how much I loved it. The New York Times passed when I was twenty-two, but sometimes I wonder if they’d take me now. The Washington Post, Chicago Tribune...I know they say print is dying, and everything will be digital or on the television, but I want to be at a newspaper again. But on the other hand, television is good as well. If Christiane can do it, I can, too. CBS, ABC, NBC, CNN, anything else with a C. One good piece in the New Yorker just isn’t enough. 

What do you think? Should I pursue journalism? Or should I wait until the book is done and published? Or should I just not go after it at all? I’m lost here, Jess, and I know I can’t depend on you to fix it, but I value your opinion. Any answer at all would help me make a decision, really. My mom says I can do anything if I try -- she’s always said that. Sometimes, though, I lose faith in the world and luck and anything else good. I could end up a nobody. I need your realism, Jess -- I can’t seem to find the balance between optimism and pessimism, not yet. I remember one time you offered to drive at me screaming in a foreign language, which was probably a joke, but I’d take you up on it if I could. I miss the guy that offered to do so. I could use support like that. 

Responding to your questions about the baby, I think I’m going to leave the sex a surprise. And I know you said you think it’ll be a girl, but honestly, I have a feeling it’ll be a boy. Just a gut feeling, but I’m pretty sure. It’s a little too soon to think about names, though. If it’s a boy, I think everyone expects me to name him Richard, but if it’s a girl? It’s a good thing I have time to decide. 

Don’t worry about Chris and Matthew. I get it. Lane wasn’t your biggest fan for a while either, and it’s admirable that they stick by your side no matter what. A lot of people would kill to have friends like them, no matter how wacky. Wait, now that you mention them, and this is a realization long overdue, but didn’t there used to be five guys working at Truncheon? You only ever talk about Chris and Matthew, so I’m just a little confused! 

I’m rereading your email obsessively to make sure I’ve answered every question and replied to every topic you mentioned. I think I have, and it’s getting late, so I’m wrapping this up!   
Eagerly awaiting your next email,

Rory. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

“It’s been good,” Rory says, compacting some snow into something resembling a sphere so she can add it to the snowman she and her mother are making -- they’re trying to recreate Cher in snowman form for the contest. “It’s good that we’re back in touch, you know? That whole email-every-three-months and see-each-other-every-four-years thing wasn’t...wasn’t enough.”

Lorelai smiles. “Well, I’m glad it’s working out.”

“It’s just…” 

“What?”

Rory looks away, blushing only slightly. “I’ve had a lot of time to think over everything, you know? The month of radio silence gave me a lot of time to just...reflect.”

Lorelai sighs. “You had another realization.”

“Yeah,” Rory confirms. “I think…”

“What?” Lorelai prompts, curious to find out what Rory has on her mind.

Rory looks back at her mother and holds her gaze. “I’m still in love with him,” she admits softly.

Lorelai’s eyes widen. “Way to bury the lead, kid.”

Rory ignores the comment. “After all these years, I guess I just buried those feelings down, hid them away...but I never stopped, really. Or maybe I did. Maybe I just fell in love with him again. All I know is that the feelings are there. All I know is…”

“That you love him,” Lorelai finishes for her. 

Rory bites her lip and nods. 

“But isn’t that good?” Lorelai asks. “You love him, and he loves you. Isn’t that what everyone strives for these days? What all the songs are about?”

“It should be,” Rory agrees. “But…”

“Honey, you’ve really gotta stop doing that trailing off thing,” her mother sighs. “I’m no love guru, but I don’t see why you’re hesitating. Or why you’re not currently in Philly making out with him.”

Rory looks away again in embarrassment. “I told him I just wanted to be friends.”

Lorelai gapes at her in surprise. “You  _ what?” _

Rory sighs. “When Jess replied to my email he said that...that he meant what he said the night of the dance marathon. ‘In another life, maybe things would be different, but they’re not,’” she explains, quoting the one line from Jess’ email that she hasn’t been able to shake off. “But he was very clear in that it was okay if I didn’t feel the same way, and being friends is okay with him, because he just wants me in his life.

“And I just...it’s too late, you know?” Rory confesses. “After all these years, all the times he’s opened himself up to me and I’ve thrown it in his face...I can’t just expect him to take me back just because the feelings are there again. It’s unfair of me to ask that of him.”

“But isn’t this him opening up again?” Lorelai points out. “This is another chance, Rory.”

Rory shakes her head. “It’s too late, anyway. I sent the email this morning.”

“Oh, babe…”

“It’s fine,” Rory insists, swallowing. “It’s probably best I just keep moving. Find someone new. Move on from all of this for good.”

Lorelai doesn’t reply right away. Instead, she stands there in contemplative silence, staring at nothing in particular. “I used to think Christopher was going to be the eternal ‘what-might-have-been’ of my life,” she says after a moment. “The one relationship I would always wonder about, if we’d made different choices. And in a way, he was, just...not the way I always believed him to be.

“After I married him and then we got divorced, it was kind of over and done with, you know? The big question had been answered. I found out then that we were never made to last. Through all that, though, there was an even bigger ‘what-if,’ and it had been there for years even before anything actually happened. Even before I realized how I felt about Luke, there was something there. A possibility that didn’t seem likely to occur. And after we broke up, and I got with your dad, and even after the divorce, Luke was this big question mark. My biggest regrets were suddenly all about him, and it was so much different than Christopher. But then...then, we answered the question for ourselves.” Lorelai meets Rory’s gaze and looks at her daughter intently. “So, the real question is, kid, who’s the biggest ‘what-might-have-been’ in your life? Who’s the one you’ll always say is the one that got away? Because  _ that,” _ Lorelai emphasizes, “might be a question you’re able to answer.”

Rory stands there in silence, contemplating her mother’s words. She knows that Christopher had been the person Lorelai couldn’t quite let go of, not until there had really been closure. Until a second chance had failed. Luke had always been there, and even though it had seemed like there was nothing left to rebuild upon, he and Lorelai had made it work. She hadn’t lost him at all, despite her mistakes. And while Rory’s relationships have always been her own, there’s something so familiar about what Lorelai described. “I feel like everything with Logan has been...wrapped up,” she begins. “The baby will always keep us connected, yes, but romantically? It’s no longer an option. I might always have some sort of feelings for him, but...but it doesn’t really hurt like I thought it would.”

Lorelai nods. “And?”

“Same with Dean, you know? I don’t feel the way I used to, but I don’t resent him. I don’t have any hangups with him, either.” Rory exhales slowly. “But with Jess…” 

She trails off, but Lorelai understands. “Moving on is always an option, yes, but so is he.”

Rory scrapes some snow off the snowman, smoothing out part of the face. “He’s just..such a good guy,” she murmurs. “The way he says that he just wants to be in my life, that being friends is enough for him, and I just  _ know  _ that he means it. I have to do the same. I have to accept that friends is all we can be, because…”

“Because what?”

“I...I’m scared,” Rory mumbles. “I’m too afraid to give it another go. ‘Cause...it was good, good when we were together, even though I let everyone convince me otherwise. But then it all went downhill so fast, and it just...shattered us. I can’t go through that again with him.”

Lorelai listens to Rory somberly, her expression anything but happy. She understands, she really does -- she just wishes there was something she could do or say to fix this. Lorelai wants Rory to be happy, and she hates seeing her daughter hurting like this.

“And yet…” Rory shakes her head. “I can’t help but wonder if he’s my great love story, you know?”

Lorelai smiles sadly. “He could be.” 

“It’s kind of perfect, in a way, how we keep finding each other, falling back together despite everything trying to push us apart. No wonder he’s writing about it. It’s the kind of story some people would kill for. 

“But If he is,” Rory says almost desperately, “then why am I too afraid to give it a happy ending?” 

Lorelai sighs. “I wish I had the answer,” she sympathizes, “but this...this is tough.”

Rory knows Lorelai is right. There’s no easy fix to this, no matter how much she craves for there to be one. Is it really too late? Has the final door been closed? Is there no way forward? She wishes, above all, that she could talk to Jess about this. But that, she knows, is an option long gone. 

-::--::--::--::--::--::--::--::--::--::--::--::--::-

Jess is sitting at his desk in Truncheon, reading one of the manuscripts that was submitted after New Year’s, when his phone rings. He ignores it at first, letting it go to voicemail, figuring it’s either spam or maybe his mother, and both can wait. It’s when it rings again that he groans and sets his work aside, picking up his phone and answering. “Hello?” He mutters, his tone a little unpleasant.

“Check the attitude,” Luke’s gruff voice says. “What’s with your ignoring my call?”

“Sorry. I was working and figured it was spam.” Jess spins his chair to face his computer again, staring at the manuscript. “What’s up?”

“How’s your schedule looking lately?” 

Jess laughs. “I’m not going to see daylight for weeks at this rate.”

Luke grimaces. “A lot of work, huh?”

“Walter White  _ wishes _ he had the kind of demand we do.”

“Who the hell is-- nevermind. Look, the winter carnival is coming up,” Luke proposes, “and I was...well, I was thinking...if it’s possible…I was wondering if you could clear up some time to, uh, visit.”

Jess sighs. “Like I said, I’ve got a lot on my plate. I’m gonna have to pass this time, Uncle Luke,” he says apologetically. “But thank you for the offer.”

“Ah, well, it was worth a shot.” Luke pauses for a moment. “Don’t keep yourself from visiting because of...because of her,” Luke urges him, somewhat awkwardly. “She wants to see you more than you know.”

Jess purses his lips. “I don’t know what you’re talking about.”

Luke sighs. “Sure, okay. Well...don’t be a stranger, Jess.”

“I’ll check in in a few days,” Jess assures him. “Whenever I finally surface, that is.”

“Okay. We’ll talk later, then.”

“That we will.”

Jess hangs up and places his phone on his desk. He breathes out slowly, and nearly jumps out of his skin when he hears Matthew’s voice behind him. 

“What was that all about?”

“Jeez,” Jess says, turning around to face his friends. “Do the  _ Conjuring _ people know about you two?”

Chris dismisses Jess’ quip. “Who was that?” He asks, hoping to feign nonchalance.

“My uncle,” Jess replies. “He’s trying to get me to go back to Stars Hollow.”

“You didn’t tell him that you  _ did,” _ Matthew says. “I’m sure that would shut him up.”

Jess rubs his eyes. “Mhm.”

“Any specific occasion, or…?”

“The annual winter carnival that the high school puts on,” Jess explains. “Not really my thing.”

Chris frowns. “You shouldn't not go because of her.”

“I promise you, I don’t know what you’re talking about.”

“Oh, bull,” Michael snaps. “Jess, this is ridiculous.”

“You know, our day-to-day lives absolutely do  _ not  _ pass the reverse Bechdel test,” Jess quips, but his friends aren’t amused.

Chris rolls his eyes. “Alright, we are taking you to the bar tonight. You need to move on if you’re not going to go see her.”

“Forget ‘moving on,’” Matthew insists. “Dude, you need to get  _ la _ \--“

Chris elbows him. “Look, Jess,” he says, his voice softer when he sees the pained expression on his friend’s face. “I know it’s tough, okay, but she turned you down. That’s closure enough. We love you, and we hate to see you torturing yourself like this.”

Matthew nods. “I know we’re crude, but if you’re not going to go back for her, or you can’t even go to the same town that she’s in because of all this, then you need to find a way to be happy, somehow.”

Jess bites his lip, avoiding eye contact with his friends. They’re right, of course, they usually are -- not that he would ever admit that to their faces, but it’s true. They’ve had this conversation a hundred different times in every way, shape, or form, but nothing ever seems to change his mind. This time isn’t much different -- their words continue to plague him, as they always do, but Jess refuses to budge. “I have to check my email,” he says gruffly, turning his chair around and tending to his laptop. Of course, there’s en email from Rory, right at the top of his inbox.

Matthew stares. “Wait, you’re emailing her?”

“Yeah,” Jess admits. “She wrote me on New Year’s Eve, I replied a few days later, and I guess this is her response to that.”

“What did she say?” Chris inquires, curious.

“I haven’t read it yet, Chris.”

“No, you jackass, the original one she wrote.”

Jess, albeit reluctantly, recounts the general message of Rory’s first email. “She apologized,” he says simply. 

Matthew whistles. “And what did you say?”

“It’s none of your business,” Jess snaps angrily. “I’m sick of talking about this. You guys need to pick up some hobbies.”

His two friends exchange glances. “Alright. Well, we’re going to the bar,” Chris relents. “Meet us there, maybe?”

“Maybe,” Jess sighs, running his hand over his chin. “Just...let me reply to this email. And  _ don’t,” _ he adds, catching his friends’ faces, “start on that.”

His friends nod and head out the door, Matthew starting to talk about something, and when the door shuts behind the two, Jess turns his chair back to face his computer. He reads through Rory’s email, a twinge in his heart as he reads what she said.

Once he’s done, he wipes his eyes and hits reply. He’s grateful that Rory is being honest, even if those weren’t the words he wanted to hear. Her words hurt him more than they help him -- he loves her, and she doesn’t love him back. Now that it’s been put in words, it breaks him more than it did when it was all undefined. 

More than anything, Jess wants to see her, to kiss her, to hold her, to  _ love _ her and have her love him back -- nothing he ever had all at once. It’s tempting to take up Luke’s offer, but the fear and his reasoning takes over too quick. It’s too soon to see her again. They’re only now talking again, and going back to the scene of what broke them the last time is playing with fire. So, he settles for an email, biting back the words he wants to say.

Dear Rory,

C’mon, Ror, did you really think I would delete your email? I’m seriously wondering if I should be offended or not. I think I can move past it, though, because I really was glad to hear from you -- I honestly wasn’t sure if you’d reply a second time or if I’d scared you away. 

There was nothing to worry about, Rory, there really wasn’t. Sure, you’ve made mistakes, but we all have. There was a time when making mistakes was all I did, but you were always there despite everything else. I didn’t deserve you then, but I still had you by my side. Don’t beat yourself up for your feelings like this. I can speak from experience, and it isn’t healthy. 

I’m not going to go into a long rant on why Fitzgerald is a brilliant author and how you’re wrong, as literary discussions are a little difficult to do by email, but I’ll save it for another time. I’m writing down the books you mentioned that I haven’t read and I’ll be sure to get to them soon and give you my feedback on them. 

I need to get back in the writing game, I know. We’re sending copies of  _ The Subsect _ to some independent bookstores tomorrow, and once the workload eases up I’ll get back to writing. I don’t know exactly what I’ll write about, though. I don’t have many concrete ideas at this point, but that could definitely change. I’m setting aside the work that caused our fight to begin with, and I won’t pick it up again unless you say otherwise. It’s really okay if you’re not comfortable with it; I understand, and I’m sure inspiration will find me again soon. I have a lot of notebooks with random things scribbled in, so maybe I’ll find something there. There are so many stories to be told, so I don’t think I’ll be at a loss for words for much longer.

On the career front, I understand what you mean. I don’t doubt that you’ll find something you love, but how much time it might take, I can’t tell you. If you want to get back into journalism, then you find a way. Don’t give up on your book, though. If you love it so much, hold onto it and finish it. I’m always here to look over a manuscript or two if you need -- which may or may not be partially a ploy just to see what you’ve been working on. Nonetheless, of course, it all depends on where you want to raise your child. If you want to raise it in Stars Hollow, then maybe teaching at Chilton is your best bet. It doesn’t have to be permanent, but it looks good on a transcript and I genuinely believe it would be a good fit for you for the time being. Teaching at Chilton isn’t a mark of failure; to the contrary, it’s a mark of success. You had a lasting impression on that school, Rory, and it wasn’t because you pulled the fire alarm or got into a fight in the courtyard. They admire you and want you to teach their students, who really tend to be the best of the best. I can picture you discussing literature in the front of a classroom, I really can. But if that just doesn’t feel right at all, and you still want to stay in Connecticut, there are definitely some papers and gazettes that will be more than happy to hire you. You don’t have to settle in Stars Hollow immediately, either. New York is close enough and it has good papers and television networks, as does Boston, Hartford, or even Philly. You are definitely not at a loss for options.

As to what I think you should do, I really can’t say, because it’s your life, not mine. I think you should consider where you want to live and how your baby will factor into everything, and then go from there. I believe in you, Ror. You’ll make the right decision. But if you still feel a little rusty, or need some refreshers, I’d be more than happy to get into my car and scream something while driving at you. As long as you jump out of the way, of course.    
Yes, there used to be five guys at Truncheon, but the other two ditched us some years back. Liam was offered a job at Penguin Random House four years ago, but he still checks in from time to time whenever he’s in town. James got a book deal with  Simon & Schuster in 2008, and we don’t really see him around much. It’s a lot more work with less of us, but it’s not bad. Liam and James just weren’t as invested in small, independent publishing, which is fine. Chris and Matthew and I are all in it for the long haul, and honestly, I don’t have any regrets when it comes to this. 

If you ever want to come visit Truncheon, we’d be happy to have you. It’s busy, yes, but without many open houses or visitors it can feel a little empty. It hasn’t changed much in the last decade, so there isn’t really anything new for you to see, but it would still be great to have you here.

From,

Jess. 

  
  


**Notes for the Chapter:**

> thoughts?


	19. The Firelight Festival

**Summary for the Chapter:**

> Decisions are made at Truncheon. Stars Hollow celebrates the Firelight Festival, where Rory finds herself facing her past.

**Notes for the Chapter:**

> First off, thank all of you for being so patient! School takes up a lot of my time, and typically drains me of motivation, so that's why it's been over a week since I've updated. I'd expect updates to be weekly, but if I'm too busy it could be longer. I'll keep you guys posted with each update, but that's what I'm thinking will happen.  
Second of all, you may have noticed that I changed the number of chapters from 33 to 30. I'm not 100% set on this number either, but I altered the plan a little bit, and currently I've planned 30 chapters. It might change again, but for now, there's only 11 more to go! Another note is that I changed formatting of the spacers, but that's it.  
And last of all -- I really hope you enjoy this chapter. It has a scene I've been set on having since the beginning of this fic, and we're finally here!  
NOTE: For the full experience, I recommend you listen to Romeo and Juliet by Dire Straits during the Firelight Festival scene(s). It's the song I picture would play if it was actually an episode, so.  
ANOTHER NOTE: This chapter takes place a couple/few weeks after the last one. I didn't want to write unnecessary scenes just to repeat them in Rory's email, so consider the first few paragraphs exposition.  
Thank you guys! <3

Dear Jess,

I’m so sorry it took me so long to reply! I didn’t plan on not writing back for two weeks, but I got swept up in work at the Gazette, believe it or not. There’s a lot of things happening here -- well, a lot for Stars Hollow, anyway. Kirk’s having a baby (god help us all), there’s a new ceramic unicorn store opening to replace the one that closed, one of Babette’s gnomes broke, and Taylor’s soda shoppe has a new ice cream flavor (he insisted that was on the front page, no surprise there). All that combined with having a staff of three lead to a lot of late nights. I’ve also been writing my book when I can, too, so you can imagine how little time I have for anything else. We went up to Nantucket to see my grandma for a couple days last week as well. It’s beautiful, and she’s so happy there, really. Did I tell you she’s a docent at the natural history museum there? Maybe not what comes to mind when one says Emily Gilmore, but she really knows her stuff!

I had some time to think about my career and living situation, and what you said. It’s a hard decision to make, no doubt about it; I think part of me has always wanted to settle down in Stars Hollow at some point. But to be fair, nothing has really turned out the way I thought it would -- which I now realize is okay. I’m off-roading it here, Jess, but I’m not too worried. I’m planning on moving to New York, like I was before I found out I was pregnant, but burrough wise? I’m clueless as to where to live. I had an apartment but I never really got to know the city. I have time, though, to figure out which neighborhood is best and to scope out some affordable apartments that can fit me and a baby. (A baby. It sounds so weird to say, doesn’t it?)

Of course, I might wait for a while to move, just because I’m going to be a single mother who doesn’t know what she’s doing. I might stay in Stars Hollow for some time first. It all depends on my job. That’s right, you heard me! I’m applying! For a steady job this time, not that freelancing thing I was trying to make work. I’m applying to CNN, of course -- besides it being a place I’ve always considered, there’s always the off chance I could work with Christiane. And even if I don’t, it’s still cool. There’s also CBS News, NBC News, ABC News, TIME Magazine, and of course, The New York Times. Outside of New York, I’m applying to the Hartford Courant just in case I decide to stay at home. It’s comforting to know it’s always there whenever I decide to settle down in Stars Hollow. There’s a couple others, but I’ll stop the listing; I know it’s excessive, but this isn’t like college. A 4.0 unweighted GPA and good SAT scores might’ve been enough then, but I’m in the real world now. However, I’ve got multiple pitches prepared, as well as several of my pieces. I even tracked down my employer at the Stamford Eagle Gazette (read: NOT Mitchum Huntzberger) to write a letter of recommendation, and my old headmaster at Chilton, too. I was underprepared before, but there’s more on the line now. I’ve even gotten my mom and Luke to run practice interviews with me. 

(I hear what you said about Chilton, though, so I’m keeping an open mind about graduate school. I don’t think it’s best to get my master’s while I have an infant, though, so I’ll put it on the back burner for now. It’s always an option, though.) 

Before I forget: something pretty cool happened when I was in Nantucket. My mom and I went into town to scope out the coffee situation, and in one café, I heard people talking about your book! Of course I had to tell them I knew you, and they said they really loved _ The Subsect. _ May this be enough to get another book out of you -- and soon. And if you want to write about us, do it, okay? I know I flipped out when I found out at first, but it was an overreaction, and I’ve definitely cooled down by now. It’s totally fine if you write it -- I promise. Who am I to deny the world the next great Jess Mariano novel? So, write it. (If you still want to.) And maybe, give it a happy ending.

Things are moving forward, and it’s such a good feeling. I feel like I’ve finally fixed everything (as much as I can). Not everything is perfect, and not everything is the way I want, but it’s in a way that I can live with. I’ve got myself back on track, and really, I owe it all to you. Without everything you’ve done for me, I could be in a very different place.

I miss you, Jess. I don’t have time to go to Truncheon in the immediate future, but I really want to visit again. It’s been a while, and I think a second run will be good for both of us. But you should come here, Jess, you really should. The town misses you. _ I _miss you. Luke said he’s been trying to get you to visit, but that you never have the time. The Firelight Festival is in a few days...you can always come in for it. Second chances and all that, right?

Anyway, this is getting unruly and bordering on sentimental, so I think I’ll cut it off here. Think about what I said, though. And consider this an informal invitation. 

Love, 

Rory. 

Jess finishes reading Rory’s email, a bittersweet taste in his mouth. Her sentimental tone is not lost on him -- the last and only time she visited Truncheon is _ not _ a good memory, nor one neither of them are proud of, and both that and the Firelight Festival holds so much weight for the two of them. 

All her words about second runs hits hard, though, and he finds himself wondering. Wondering _ what if, _ which isn’t anything new, but it’s stronger, more hopeful, due to her words. Jess _ hates _ how she holds this power over him, how she’s able to raise his hopes and then send them tumbling down in one split second. What does she mean by second runs? Is there more weight to her words than she’s letting on? Can he hope for another chance himself?

Even if there is a hidden meaning, though, even if she’s hiding something, her invitation is not enough to send him to Stars Hollow. Jess loves seeing his family, and he loves seeing her, but going back to the town now after what feels like so many failed attempts fills him with dread. He’s about to click reply, as if to reply no to an RSVP, but--

“Good news!”

Jess turns from his desk to see Matthew, breathless from running down the stairs, waving around his phone like a maniac. 

“What is it?”

Matthew beams, looking between Chris and Jess excitedly. “Remember the brownstone we looked at for Truncheon first?”

“You mean the one in the village in New York?” Jess asks. “The one that we couldn’t afford even if we’d sold all of our worldly possessions?”

“That’s the one.”

Chris doesn’t look up from his work. “What about it?”

Matthew’s grin only gets wider as he looks at the other two triumphantly. “We got it.”

Both of his friends stare at him incredulously. “What?” 

“The current owners must’ve got sick of it or something, I don’t know, but they’re selling it! For a _ very _ reduced price, might I add, so I put in a tentative offer, and they accepted!” 

“When’s it ours, then?”

“They move out in March,” Matthew explains, “and we get it the 30th.”

Jess smiles to himself. He loves Philly, he really does, but New York was always his home. And besides, this is an opportunity too good to pass up. “Take a vote?” He offers, even if he’s sure it’ll be unanimous. 

“All those in favor of moving to New York, say…” Matthew trails off, trying to think of a word.

“How about we just raise hands?” 

“Fine. All those in favor of moving to New York, raise your hand.”

All three raise their hands.

It’s funny, Jess thinks, how life goes. How one minute he’s avoiding the girl he loves, but the next, he’s going to move to the same city she is (or plans to). He pushes it aside, though, when the phone rings. “Truncheon Books,” he says offhandedly, opening a manuscript he’s supposed to read.

“Jess!” Liz’s voice exclaims from the other end. “How’s it going, kid?”

Jess grimaces. Even after all these years, talking to his mother still puts him on edge. He’s not angry like he used to be, but thinking about the childhood he had with her (or, rather, without her) doesn’t exactly put him in a good mood. “It’s going,” he says non-committedly. “What’re you calling about?”

“I can’t just call my boy to see how he’s doing?”

“You can, but you don’t. What’s up?”

Liz sighs. “I really am just checking up on you, Jess. We haven’t seen you for a while, you know, and you left under...under mysterious circumstances, to say the least.”

“I don’t have to run my comings and goings past all of you.”

“A goodbye is always nice,” Liz says. “You usually let us know.”

Jess laughs under his breath and runs his hand down his chin. “Old habits die hard, I guess.”

Liz pauses for a moment before she replies. “Is everything okay?”

_ A question thirty years too late, _ Jess finds himself thinking bitterly. Liz’s concern isn’t lost on him, but this reformed version of the woman who just couldn’t bother to put in any effort into raising him? She’s not the mother he knew. And while he doesn’t _ hate _ her, and might even _ love _ her at times, rare as they may be, it’s still not enough. That resentment, how small it may shrink someday, will always be there. He takes all her words with a grain of salt immediately; he can’t help but remember all the times he wishes she’d asked if he was okay, but wasn’t paying close enough attention. “I’m fine, Liz.”

“And you’re sure? Luke says you keep turning down his invitations.”

“Positive. In fact, Chris, Matthew and I just got some really good news.”

Liz excitedly demands he tell her.

“Truncheon is officially moving locations,” he informs her. “Matthew put an offer down on a brownstone in the village.”

He can hear the smile in Liz’s voice when she replies. “That’s great! Luke will be so proud...and _ I’m _ proud. I always knew you were gonna be okay.”

_ Really? _Jess bites his lip, but the words spill out anyway. “Did you think that when you sent me to live with Luke? When you didn’t want me to come home for winter break? When you gave up on me?” His voice is quiet; the words he’s been harboring for so long come out choked and broken. 

Liz lets out a deep sigh. “I never gave up on you, Jess...I was so young when I had you. I had no idea what I was doing. It’s not an excuse, but we can’t all be Lorelai Gilmore.”

“Yeah, well…”

“You turned out great, with no thanks to me. If you stayed with me...I don’t know where you’d be. I grew a _ lot _ when I met T.J., you know. He was what I needed to really grow up and get myself together.”

_ Your kid wasn’t motivation enough? _

“T.J….he brought out a side to me I didn’t know existed. There are people in our lives, Jess, people that we didn’t see coming, but people that still save us.”

“Very introspective for Liz Danes,” he mutters, but he finds himself drained of animosity. 

She laughs. “I’m getting sappy, I know. But I hope...I hope that one day, you can forgive me.” Pause. “And I hope one day, you can forgive yourself, too.”

**

After his phone call with his mother, Jess can’t help but repeat her words over and over. _ There are people in our lives, Jess, people that we didn’t see coming, but people that still save us. _

_ And I hope that one day, you can forgive yourself, too. _

Maybe she’s right, he thinks. Rory was the one who -- well, she didn’t _ save _him, not quite, but she inspired him, she motivated him, she turned his world upside down -- the one he never expected. He hasn’t forgiven himself for her, either -- for falling for her, for hurting her, for letting it all fall apart in the blink of an eye like she wasn’t important. There’s a chance Liz is right, he knows, even if he doesn’t like it. 

“Even a broken Liz is right twice a day,” Jess laughs to himself under his breath.

Chris looks up from his work. “What?”

Jess waves it off. “Nothing.”

It’s not nothing.

It’s so far from being nothing -- countries, continents, oceans, lightyears from it -- so far that its eye-opening, world turning, and hits heartbreakingly close to home. 

_ I hope that one day, you can forgive yourself, _she said.

Maybe it’s about time. 

**

The Firelight Festival is in full swing, and a Stars Hollow winter has never appeared more beautiful. 

The town is blanketed by a light layer of snow, which sparkles as though it’s made of crystals. The gazebo, trees, and buildings are wrapped in fairy lights, and the usual stars are strung from tree to tree. The town bustles about from cart to kiosk to cart/kiosk, listening to the troubadour and his guitar. The sun is down, but the town is perfectly illuminated -- and for Rory, it carries a memory, one that weighs her down, down, down, as she walks through the town square with her mother. 

Everything they pass reminds her of that night. Passing through the line for the burger cart, she remembers meeting his gaze, and the look that was on his face -- heartbroken and hopeful all at once. Each step she takes is an echo of the ones she took when they ran through the streets, running from something resembling reality. Glancing over at Gypsy’s, she feels the same way she did when she watched him drive off, his words still echoing in her mind.

Lorelai glances over at her daughter, concerned. “Rory, honey? You okay?”

Rory nods. “Why wouldn’t I be?” The words taste bitter on her tongue.

They stop at the bonfire where Luke, Liz, T.J., and Doula are waiting. Liz has a cup of punch (Miss Patty approved punch, of course), and T.J. has his arm around her shoulders. Doula is talking to Luke, who looks grateful when his wife comes over and redirects Doula’s rambling to herself. Rory turns from the fire for one moment, the chatter of Doula, Lorelai, and Liz barely registering.

That’s when she sees him. 

He stands eerily close to where they stood the last time, hands shoved in his coat pockets, an apprehensive look on his face. Their eyes meet, and the tenderness of his gaze is almost enough to make her turn back around.

Almost. 

Rory slowly approaches Jess, and he walks towards her. His guard is up, she can tell -- although his face is slightly pained, she knows he’s trying to hide it for her benefit.

“Hey,” she ventures, choosing to stare at his shoulder instead of his eyes.

“Hey,” he replies. 

She shifts awkwardly. “I didn’t think you would come.” 

It stings a little, but it’s honest. 

Jess shrugs. “Turns out I could make it.” He doesn’t embellish.

“So…” Rory searches for something to say, _ anything, _ just to ease the tension between her and Jess. Emailing with him was one thing, easy, simple, but talking to him in person for the first time in two months? She decides on the default small talk. “Work’s good?”

“Work’s good,” Jess confirms. “And you? Everything’s...good?”

“Yeah,” Rory breathes. “Everything’s good.” She glances up at him to see his expression has softened, if only slightly. 

“And the book? It’s going well?”

Rory nods. 

The corner of Jess’ mouth quirks up slightly. “Good.”

Rory bites her lip, fidgeting with her hands. Him standing in front of her brings everything back to the surface, to the point where it borders on overwhelming. “Jess, I…”

Jess smiles sadly. “It’s okay, Ror.” His eyes say what he is not willing to, but Rory hears him more than she ever did before. 

“No, it’s not,” Rory says a bit more firmly. “I just...I…” The words are there, right on the tip of her tongue, but she can’t get them out. Instead, she trails off, standing in front of him, both of them silent in an odd form of a stalemate. 

All she can think is that he _ loves _ her. She can hear his words from two months before, and she can see it in his eyes as well. She can hear it in the gentle way he speaks to her now -- the voice of someone who’s just so tired of hurting. 

Jess exhales slowly and stares down at his shoes before he looks back up at her and speaks again, trying to keep the moment light and less uncomfortable. “Y’know, I was talking to Matthew the other day, and he was saying that Kerouac was--”

“Jess.” 

He blinks at her, staring at her expectantly. 

“I...why did you come back?” She asks weakly, but she thinks she already has the answer. 

Jess takes a moment to answer, blinking a bit, his expression reminding her all too well of a spring afternoon years ago. “I came back for you,” he says, and it’s simple, but it’s also anything but.

Fourteen years ago, he wouldn’t admit to the real reason he came; too scared to, too afraid to put himself out there; but now, now that he’s saying the words that she’d wanted to hear so long ago, she finds herself falling into the same familiar steps.

So, she breathes in, takes the plunge, and kisses him. 

**Notes for the Chapter:**

> "When you gonna realize it was just that the time was wrong?"


	20. Places We Won't Walk

**Summary for the Chapter:**

> Jess and Rory have a talk that is long overdue.

**Notes for the Chapter:**

> This chapter is ungodly long (roughly 6.7k), but it kinda got away from me. There's some real good shit here though if I'm honest

Her first thought: his hair’s a lot longer than it used to be.

She laces her fingers through it, like she used to do when they were younger; they’re older now, more secure and self assured, so it’s different, kissing him, than it was then, but it’s not unfamiliar at all. 

When she first kisses him, he freezes, caught off guard. After a few seconds, though, he melts into it; Jess wraps his arms around her waist and pulls her closer, needing the warmth of her body against his. He kisses her desperately, passionately, like he’s missed her for an inordinate amount of time.

Which, she realizes, he has. 

His kiss is still unrelenting and urgent, and something about him makes her feel dizzy and weak in the knees. He pulls her closer, if that’s even possible, holding her flush up against him until there’s no air between them. 

They pull away only to breathe, and even then Rory feels like all the air has been sucked out of her lungs. His eyes are bright as he holds her gaze, his arms still wrapped around her.

“I love you,” she murmurs, breathlessly, quietly; the words are only for him to hear.

“I love you, too.”

She wants to pull him in for another kiss, but she holds herself back. She knows they’ve probably attracted a crowd, and it’s only a matter of time before people start asking questions. 

(But she can’t tear her eyes away from him; no surprise there.)

It doesn’t feel real, standing in the middle of the street in his arms, being held like this by him after so long. But it’s real, he’s here, he’s here, he’s _ here, _ and so is she, and nothing is keeping them apart this time. 

As much as she wants to continue this, to kiss him until the world falls away, she knows they have to _ talk, _ and she wants to preserve this moment, keep it just as magical as it feels right now. This moment is just for them -- even if it’s theatrical, a private show for the entire town, and something that will surely feed the rumor mill for a week. 

It takes all the willpower she has to step away, just enough so that his arms are still around her, but she won’t be tempted to kiss him.

(That’s a lie. She wants to kiss him again more than anything.)

“We’ve attracted quite the audience,” Jess laughs.

She smiles. “It’s the show they’ve all been waiting for.”

(Read: It’s what _ I’ve _ been waiting for.)

(He knows.)

“I should go,” she whispers.

“Do you want to?”

“No,” she admits. “But I should.”

He nods. 

“Can we...can we talk tomorrow?” Rory asks softly. “I want to keep this moment just like this.”

“Of course.” He tucks a loose curl behind her ear. “But first…”

He leans in and kisses her again. It’s slower, softer, deep but still gentle. Her heart flutters in her chest, even when he pulls away. “Get out of here,” he murmurs, the soft smile on his face unrelenting.

She doesn’t _ want _ to walk away, the way she did so often back then, but she manages to tear herself away from him and float all the way home, followed by a shocked and surprisingly speechless Lorelai.

She doesn’t think her feet will ever touch the ground again.

**

Jess stands in the middle of the street as he watches Rory turn the corner and disappear. But it’s not a bad feeling; on the contrary, this is the happiest he’s felt in ages.

It doesn’t feel real -- the feel of her lips still lingering on his, the way his hair is definitely askew from her hands running through it. Her words are still ringing through his ears; they are words he’s wanted to hear for a very long time.

Ignoring the shocked gazes of the town surrounding him, Jess turns and walks away. He slips inside the diner, leaving all of Stars Hollow to wonder what the hell just happened.

(He barely knows himself.)

**

Rory goes home, telling her mother she’ll answer all her questions in the morning, and goes to bed, but she’s too wired to sleep. The adrenaline from kissing Jess is still coursing through her veins, making it impossible to get any rest. 

After awhile of lying in bed and staring at the ceiling, Rory can’t take it any longer. Though she’s so happy and excited, the doubt is starting to set in. There’s so much they need to talk about, so many things that need to be aired out, and waiting has become impossible. So, Rory pulls herself out of bed, throws on jeans, a sweater and boots, grabs her jacket, and sneaks out the front door. 

**

Luke really should find a new hiding place for his spare key.

It takes Rory no time at all to take it from the top of the door and slip inside the diner, flinching at the sound of the bell chiming the second the door opens; it’s jarring in the silence of the night. 

She climbs the stairs, taking the same steps she did years ago. Once she reaches the top, she raises her hand, poised to knock, but before she can, the door swings open.

Jess flinches when he sees her hand; Rory snorts in amusement.

“I was just coming to see you.”

“Yeah?”

Jess nods. “I guess I’m just a little impatient.”

Rory shrugs. “I am, too.”

“Well...wanna come in?”

He holds the door open for her and she walks through, looking around the room absentmindedly. “Do you have any coffee?”

He smirks. “You never cease to stay in character.”

“I’m not a Gilmore for nothing,” she laughs.

“There’s no machine up here,” Jess informs her, answering her previous question. “The only one is down in the diner. I can go make you a cup if…” He trails off, but his offer stands.

Rory shakes her head. “It’s fine. But thank you.”  
He nods. 

Jess pulls a chair out for her to sit in, which she does with a grateful smile. He takes a seat across from her; his smile has faded slightly, but he doesn’t look unhappy. On the contrary, there’s a look in his eyes that she hasn’t seen in years. 

Rory starts pulling her sweater over her hands; an old anxious habit of hers that she was never quite able to break. “So.”

“So.”

“We kissed.”

He smiles a little wider. “Well, you kissed me.”

“And you kissed me back.”

His gaze doesn’t waver. “That I did.”

Rory can feel her face growing warm. Even after all these years, there’s just something about him that does this to her. “And I -- well, I thought -- as great as it was -- and it was really great -- we definitely need to talk.”

Jess has an amused look on his face, and Rory scowls at him for it. “Oh, shut up.”

“No, I like your rambling,” he assures her. “It’s cute.”

“I think you even said it was sexy once.”

“That’s very possible.”

“But…”

He nods, his air of happiness disappearing a bit. “We need to talk.”

“Yeah.” She exhales slowly. “It’s been a while since...a lot of things have happened.”

“Yeah.” Jess sighs and runs his hand down his chin while Rory stares at him uncertainly. “Go ahead,” he assures her. “You should go first.”

“Are you sure?”

He nods.

Rory stares down at the table for a moment, attempting to gather her thoughts. She’s had so much to say for so long, but now that he’s here -- he’s _ here, _ ready to listen, willing to hear everything she has to say -- she finds it hard to get the words out. “You left,” she begins, her voice soft. “you left. And I…

“After our first fight, after you got the black eye, when we’d made up...we were in a good place. I thought we were at a place where we could move forward. It was serious. _ I _was serious about you, Jess. So much that I…” She turns pink and doesn’t finish the sentence.

He frowns. “So much that you what?”

“Nevermind.”

“Rory...I know I’m one to talk, but this isn’t going to work if we don’t lay everything out for each other,” Jess murmurs. “It’s important, even if it’s hard.”

Rory closes her eyes and swallows, nodding her head. “I know. You’re right. I just…” She doesn’t meet his eyes. “I was so serious about you, Jess. I thought we’d found...that we’d found _ it. _ So much that I was genuinely ready to have sex with you. And that was a big deal for me, back then, because I’d never...and my mom told me that my first time should be _ special, _be with someone that I trust, who respects me, and...I was ready for it to be you. Then everything just fell apart, and it just…” 

Jess nods slowly as he drums his fingers against the table. “We missed our chance. The timing...it didn’t work out.”

“Can we blame it on timing?” Rory asks weakly. “Or were we just...would it have been a bad decision?”

Jess hesitates before he answers. “It’s not _ blaming, _ really, but I think we were both in such uncertain places in our lives that we wouldn’t have been able to make it work back then. I don’t know if us sleeping together would have changed that.” He sighs. “But...for the record, I was ready for it, too.”

She blushes again. “We had something so _ real, _ Jess, I think it scared me. How different it was from what I had with...with Dean...it was new territory. And everyone telling me how bad you treated me...it didn’t help.”

Jess’ expression darkens. “Ah, yes. The golden boy.” He shakes his head. “I wasn’t the best boyfriend.” 

“You weren’t,” she admits, “but you didn’t get credit for the things you did that were _ good.” _

“Oh?”

“Like...I know you weren’t always reliable, but you cared. Buying us tickets to the Distillers, looking up how far from Yale was from Stars Hollow…”

Jess chuckles. “That wasn’t that big of a deal.”

“It was. For you. And I knew that. It didn’t...it didn’t go unnoticed, Jess. It meant a lot to me that you had faith in us, that we would last when I went to college. After all of Dean’s talk about how we might have to break up when I went...it meant a lot to me that your first thought was the distance, not us breaking up.”

“I don’t know if I ever believed we would make it,” Jess sighs. “I didn’t have enough confidence in myself. Part of me always thought you would leave me for…”

“For Dean.”

He nods, his expression pained.

“I shouldn’t have compared you to Dean like I did. I know that now. I just...back then, he was the only other boyfriend I’d ever had. I didn’t get that it was okay that you were different, even if it was really stupid of me to expect us to be like me and him. It was unfair of me.”

“I had a lot of insecurities back then, and a lot were about him. I was…” He breathes in and out slowly. “I was jealous. I didn’t want to admit it then, but I was. The comparisons only made it worse.”

Rory bites her lip. “I should’ve trusted you more.”

“I should’ve been more open with you.” He sighs. “Even if it was hard.”

“I should’ve focused on the good. You trusted me. Even if you hated me being friends with Dean, you still _ trusted _ me.”

Jess shrugs. “It was the bare minimum.”

“No.” Rory shakes her head. “Dean never trusted me like you did.”

Jess smiles a bit, but it’s gone as soon as it appeared. “Okay.”

“I think I had it all wrong back then,” she admits. “I thought Dean was this reliable, consistent guy, but--”

Jess snorts. “If you’re about to say that I was reliable, I’ve got some news for you. I wasn’t.”

“Maybe not all the time, but I didn’t give you enough credit when you were,” Rory sighs regretfully. 

Jess smiles sadly. 

“But then it all fell apart,” Rory continues, beginning to get a little choked up. “And it...the party…”

Jess grimaces. “Not my best moment.”

“Nor mine, either.”

“I wasn’t mad at you for...I would never…”

Rory reaches over and takes his hand, ceasing his absentminded drumming. “I know.”

He shoots her a grateful look. “That was kind of the end of it all, wasn’t it?”

“I think so, yeah.” She squeezes his hand. “You left so quickly after.”

Jeff sniffs a bit, and Rory suddenly notices the shine in his eyes that isn’t usually there. “I thought…” He takes another deep breath. “I couldn’t graduate. I flunked out. When I told Luke...he told me to go.” He stares down, unable to look her in the eyes. “I couldn’t face you after that.”

“Jess.” He looks up at her, and the look on his face breaks her. “I would’ve been there for you.”

“I didn’t get that then.” Jess bites his lip. “I do now.”

“But...you left,” she repeats, unable to phrase it any other way. “That..that kind of thing stays with you.”

Jess winces and lets go of her hand. “I know.”

“When I see you, I still think about all the nights I spent in hostels that summer. shaking from holding back tears, trying so hard not to cry because I’d promised myself I would leave you in the past, that I was moving on, and my mom was one bed over. That kind of hurt doesn’t go away overnight.”

Jess nods. “I know. I’m...I’m sorry, Ror.”

She can see the tears in his eyes, and she wants more than anything to reach out and wipe them away. Instead, she holds herself back, knowing it’s important to say everything she needs to. “Everything after that...we kept finding each other, time and time again. But...you telling me you loved me...that threw me. And when you asked me to run away with you…I don’t know. It just...it was hard to hear. I’d basically convinced myself I’d moved on, that you didn’t mean anything to me anymore, but each time you came back that year, I started to realize I was wrong.

“But after that? You saved me, Jess. I wouldn’t have gone back to Yale without you.”

“You would’ve.”

Rory shakes her head. “I really don’t think so. I’d fallen really far down, Jess. I was in a really bad place, but I hadn’t even realized...Logan told me it was fine. And I believed him.

“But when I came to Truncheon…” She winces. “I was at a low, then, too, but in a different way. I was hurting, after Logan cheated on me, and I got the invitation, and...I don’t know.”

The look on his face hurts; the pain the memory brings him, but how hard he’s trying to fight it. 

“I led you on. I knew I was, but I did it anyway. When you asked if everything was fixed, I should’ve...I should’ve told you, that I was with Logan, but I just…I don’t know. I guess I wanted to get back at him, but I shouldn’t have done it at your expense. It was stupid and selfish and insensitive.”

“It was,” Jess agrees. It’s sharp and honest, and it stings a little, but Rory knows he’s right. “But I forgave you for it. There was never any doubt that I wouldn’t.”

“Why?” Rory nearly whispers. “Why did you forgive me?”

Jess pauses. “You made a mistake,” he says finally. “I myself have made plenty at your expense. I figured...I figured it was payback, in a way, getting what I deserved. We’ve gotten so used to breaking each other’s hearts that it was second nature by that point.”

“I wish it didn’t have to be like that.”

“We have another chance now,” Jess says firmly. “We can learn from our mistakes instead of repeating them.”

“It’s hard to let go of the past.”

Jess chuckles mirthlessly. “God, don’t I know it.”

“That’s all I really had to say,” Rory mumbles. “Your turn.”

Jess sobers up immediately, quiet; the silence unnerves Rory, but she lets him gather his thoughts, understanding that opening up has always been somewhat of a roadblock for him. 

“I liked you from the moment I met you,” Jess murmurs thoughtfully; he’s begun drumming his fingers against the table again. “It was the first time I’d ever felt like that. The only time, really.”

“I was the first?” Her voice is barely audible. She’d had her suspicions, but the truth is, Jess had never told her if he’d ever been with anyone else. 

Jess nods. “I’d _ been _ with girls before -- in that department, you weren’t the first. But I never really felt anything for them, and they didn’t feel anything for me. I started hoping that you might feel the same way, entertaining the fact that maybe I could be happy with someone else. I’d never really thought I could.” He stares down at his hands, picking at one of his fingers. “When you introduced Dean as your boyfriend, that hope went away. Even when I was ‘trying to get you--‘“ he uses air quotes here, “I didn’t think I would ever be that lucky.”

“Then why’d you do it?”

Jess shrugs. “I was already public enemy number one, so I figured, what’s the harm? Giving Dean a hard time was fun, and I had this idea in my head that since you were never going to fall for me, there wasn’t any harm in flirting. Faulty logic, but, hey. I was a kid. You were the only person in that town that didn’t hate me--“

“Luke didn’t hate you.”

“I thought he resented me,” Jess admits, “and I resented him. You were nice, we had things in common, but not too much that we could never debate on anything. It wasn’t boring. It was...exciting.”

“You liked me from day one?”

“Pretty much. I didn’t know you when I first met you, but I got to know you. And the more I learned about you...the more I really fell in love with you.”

Rory flushes pink and ducks her head. Hearing him talk about his feelings for her so bluntly makes her feel like a teenager all over again. “When did you realize?”

“Hm?”

“When did you realize...realize that you loved me?” She tucks a lock of hair behind her ear. “When did you know?”

Jess smiles softly. “I think I kind of knew all along, just...didn’t want to admit it. The feeling was there for a while before I ever put a name to it; gradually growing stronger. To quote the great Jane Austen: ‘I cannot fix on the hour, or the spot, or the look or the words, which laid the foundation. It is too long ago. I was in the middle before I knew that I had begun.’”

Rory bites back a smile. 

“But the moment I couldn't deny it anymore...that was when you kissed me.” 

She remembers that day all too well, as much as she’d tried to erase it. “And then _ I _ left.”

“It hurt,” Jess says. “It did. I’d told myself for months that it was all in my head, but then you kissed me and ran. No word for months, leaving me to go from shocked to excited to devastated. That kiss was…” He shakes his head and smiles sheepishly. “That kiss was the most...passionate I’d ever had. I knew that it wasn’t just because of how I felt. But when you stayed with Dean and never wrote, that hurt for different reasons than I’d been hurting before any of that happened.”

Rory nods. “I’m sorry.”

“No reason to be anymore.”

“I still am. I never apologized for it, anyway.”

Jess shrugs. “Even after that, I never thought we’d ever be together. I thought you...I thought you didn’t care about me. And I didn’t blame you for that. It was just the way it was.”

Rory looks down. “I always cared about you.”

Jess sighs. “I didn’t think so then. I was with Shane because...because it was easy. There was no pressure, nothing on the line. We treated each other like shit, because we were really only in it for sex.”

Rory freezes; something inside her clicks. She’d had suspicions back then that Jess had been sleeping with Shane -- what else could it have been? -- but like many other things, it had never been confirmed. “You still made sure to break up with her before anything happened between us.”

“It wouldn’t have been right not to.”

Rory darkens at that.

Jess’ eyes widen as he realizes why. “I didn’t mean -- no. It was just...I can’t excuse anything you did, but I’m not writing you off for it, either. I just didn’t feel right about it, probably because I knew how it felt to be kissed by someone who was with someone else.”

“Which time?” Rory mumbles bitterly.

“Rory.” She looks up at him hesitantly; he holds her gaze firmly. “We have to air out the past so we can move forward, but you don’t need to keep beating yourself up for it. It happened. It won’t again. That’s enough.”

She nods.

“Being with you...I never imagined I’d be that lucky. But while I was so happy because you returned my feelings -- to what degree, I didn’t know -- I had issues. I felt abandoned by my mother, neglected, I was afraid to get too close to you...that’s why I never told you I loved you when we were together. What we had, no matter how deep it went, it felt too fragile. _ I _felt too fragile to risk it like that.”

“I should’ve told you,” Rory mumbles. “There were moments where I knew I was falling in love you, but I never said anything. I was scared, but I’d done it before. I should’ve told you.”

“We were both too afraid, insecure, uncertain...I think us falling apart was inevitable. No matter how much I loved you, wanted you, didn’t want to ever let go...I was unable to communicate any of my insecurities or feelings. Not just to you, but that’s when it mattered most. And I just...couldn’t.”

As much as Rory wants to believe that they could’ve made it work then if they’d just tried a little harder, Jess’ words strike a chord. If he doesn’t think he would’ve been able to open up, maybe he’s right. But she wants to believe that if they’d just had more _ time, _if things hadn’t fallen apart...she tells him as much, and he shrugs.

“Maybe. But dwelling on what didn’t happen won’t do us any good.”

He’s right. 

(He seems to be right a lot these days.)

“After the fight with Dean, I thought...that was it. There was no going back. I’d royally fucked up, and I just assumed that that was my last chance. That I’d never...that _ you’d _ never forgive me.”

“I would’ve.” Beat of silence. “I did.”

Jess’ expression is grim as he continues. “I guess I just didn’t let myself risk finding out if you would. After my father came--“

“Your -- he _ what?” _

Jess sighs. “My father came to visit the night I told Luke I wasn’t graduating. Luke knew he was in town and didn’t tell me. I was angry and hurt and I knew I had failed him, and I was going to turn out just like Jimmy...without, you know, knocking someone up,” he adds grimly. 

“You didn’t, though.”

“I would’ve if everything that happened in the next years _ hadn’t _ happened. Luke pushing those self help books on me, you turning me down, I wouldn’t have become who I am now if that hadn't happened...but I’m getting ahead of myself.

“I decided to find him in California. I didn’t have a place to stay anymore, I thought we were as good as over...I’d become everything you didn’t want from me. The one thing I could do for you -- taking you to prom -- I couldn’t even do. So...I left. I thought it was save you a lot more hurt than a goodbye would.”

“It didn’t. Save me any hurt, I mean.”

“I know that now. But back then, I thought I was bad for you, that even if me leaving hurt, it would hurt less than a goodbye would, because you could be angry, and you could hate me like you were always supposed to. I’d been told for ages that I wasn’t good enough for you, so I believed it.”

Rory bites her lip. “I’m sorry, Jess.”

It’s his turn to reach out and take her hand. “Don’t be.”

He doesn’t say _ it’s okay _ or _ it’s fine, really _ or anything else along those lines -- _ don’t be. _ It’s because it’s not okay, not really, the way she and the entire town made him feel, the way he left; instead, even if it isn’t okay, even if it isn’t fine, it’s in the past. Moving forward is what’s important; discussing the past, getting it all out in the open so their mistakes won’t be repeated. 

Jess takes a deep breath before he continues; she knows it’s only harder as he goes on. He faced more pain as he got older, and she’ll never forgive the world for that. “I stayed in California for a while. I was still angry at Jimmy -- I probably always will be, at least a little -- but we settled into a good dynamic. Sasha -- his girlfriend -- was patient, especially when he wasn’t, and her daughter, Lily, was sweet. She got attached to me very quickly. I still talk to her.” 

Rory smiles. She likes this insight into his life, the answers that fill in the blanks he’d left for her all those years ago. 

“I left after a little while. I got restless, so I traveled. I took buses, mostly, some trains, hitchhiked once or twice. The 21st century Kerouac. I started talking to Liz again, but only out of necessity. I wasn’t in a place where I felt like I could forgive her. I was hurting, still, and I hated myself for it. I told myself I’d never see you again, and that was best; I told myself that so much I started to believe I didn’t _ want _to.

“But when Liz told me Luke had my car, I went to get it. I was tired of paying for buses or asking strangers for a ride, and it was _ my _ car, something I’d earned, that was _ mine. _I figured I’d be in and out; I wouldn’t have to see you and you wouldn’t have to see me. But then it broke down, and I was stuck there overnight…”

“I saw you,” Rory murmurs, “that night. My mom and I were walking by and I saw you sleeping in the car.”

(There’s a tick in Jess’ jaw when she says this, she notices.)

“Unintended consequences,” he mutters. “I tried to stay away from you.”

“You were angry,” Rory recalls. “You left as soon as you

saw me, both at Weston’s and the bookstore.”

Jess shakes his head. “I wasn’t angry. I thought that staying away from you was the best thing for both of us, that any prolonged confrontation would make things worse. I knew from -- when I left Gypsy’s that morning, I saw a girl I _ thought _ was you, until Gypsy told me you cut your hair, and it hurt so much that I didn’t even want to think about how much seeing _ you _ would hurt. Or how much it would hurt you.”

Admittedly, it feels good to tell her everything, even if he’d been so scared to so many times. Jess supposes there’s a difference, though, between now and all the times he couldn’t get himself to tell her the truth. Now, she’s been honest, and she _ wants _ to hear him; none of it feels unnecessary or invasive. Looking back on all the pain from his youth hurts, yes; recalling heartbreak does that, but that’s how you know that you’re still here. 

“When I saw you at the festival, something was different. I don’t know what, or why, but it was. I was trying to find Luke to give him back the money he put in my car, but I saw you and something clicked. I didn’t have some grand speech planned out, I wasn’t sure what I would say if you let me talk...after I caught up with you, and everything you said..it clicked. I loved you, and I wanted you to know.”

“Why did you run?”

Jess bites his lip. “I was too scared to see how you’d react. At nineteen, I could count on one hand how many people I’d said those words to, and I was so convinced that you hated me that I couldn’t wait around for the rejection.”

Her head is going to hurt from all the nodding she does, but Rory doesn’t know how else to show she understands. “I don’t know what I would have done if you hadn’t driven off,” she admits quietly. “I’d buried those feelings so far that I don’t think I’d have said it back.”

“I never would’ve expected you to.” Jess’ voice is gravelly again, choked up; it hurts Rory to hear him like this. “I just...wanted you to know.”

She gives Jess a little smile, which surprises him; it’s kind and gentle and understanding, a reaction he never expected when talking to her about their past, especially this moment. “When Dean first told me he loved me, I couldn’t say it back, so he freaked out on me and broke up with me. It means a lot to me that you didn’t do that.”

“Even if I ran?”

“Yeah,” she confirms. “Even if you ran.”

He returns the smile, but she can still see he's holding back tears, same as her. As good as it feels to get it all out in the open, it still hurts.

(It hurts a lot.)

Jess wipes his eyes with the back of his hand and clears his throat. “The next time I saw you, asking you to run away with me...I just wasn’t thinking. If I’d had a clear head, I would’ve realized that asking you to leave Yale, your friends, family, for an undetermined amount of time was ridiculous. But I’d just read all those books and I knew that for any chance at reciprocation I had to be open and honest. I was in a bad place then. I think I was just…”

“Desperate,” Rory offers. 

Jess nods. “Desperate to show you that I didn’t hate you, desperate to hear you say that _ you _ didn’t hate _ me, _ that you wanted me, too...desperate to be loved.” He clears his throat again. “Something I’d never really let myself feel before.”

Rory says nothing; she squeezes his hand instead. 

“I don’t know. I was just...I’d been hurting for so long, and a trip to Stars Hollow felt incomplete without seeing you.”

“I didn’t…” Rory swallows. “I didn’t...turning you down like that...it hurt me, too. I felt put on the spot, and my reflex was to say no to you, to forget you, even if I...even if I still had feelings for you. After that, though, I just...I went back to forcing myself to move on.”

Jess watches her for a moment before he speaks; she notices he looks a lot less pained than he did at first. 

“As much as that night hurt, it’s what I needed to get back on track. It was the final push, I think. Because I wanted so hard to be someone you could rely on, and I confused being ready to mature with being matured already.”

Rory remembers the heartbreaking strain in his voice that night -- _ I’m ready for this, you can count on me now. I know you couldn’t count on me before, but you _ can _ now, you _can! It’s enough to make her want to cry, just as it was then. 

“It pushed me to get my act together. I went back to New York, found a new apartment, got a job as a bartender...I started writing _ The Subsect. _It was because of you that I faced my past and turned it into a story. I’d spent enough time distracting myself. But even then, I considered taking our love story and putting it in, but I decided it couldn’t be the main focus. I wasn’t ready, I doubted you would be happy about it...but if you look closely, it’s still there. Just...more subtle.”

(Rory wonders how could have she missed that.)

(She’ll have to reread it when she gets home.)

“I wrote about my relationship with Luke, with Jimmy, with Liz. Made it about someone else, someone like me but not quite. And--“

“Blue,” Rory interjects. “The girl named Blue.”

“That’s you. Or, rather, inspired by you.”

“Man, you must’ve been really subtle if _ I _didn’t notice.”

Jess laughs. “Maybe you didn’t want to.”

(Huh.)

(He has a point.)

“The note the main character keeps checking that she wrote...that symbolizes how I pushed you to do your best.”

He nods, amused.

“And the references to ‘’many goodbyes’ and how the main character has lost Blue forever…”

“As much as I’d love to discuss my choices as an author, maybe we can save it for later,” Jess chuckles, and Rory blushes.

“Right. Sorry.”

“No need to be,” he replies, still smiling. He’s cheered up, if just for the moment; he sobers up as he continues speaking. “The next time I saw you, when you were at your grandparents’ house. I was so happy to see you, so happy to be welcomed by you, as a friend, that I didn’t really notice what was wrong at first. There were red flags -- I didn’t push on them, though, because I was so happy to see you. We were older and I don’t know, I was in a good place so I hoped…” He snorts, shaking his head. “I got my hopes up. Like an idiot, of course, but I started hoping maybe there’d be a chance for something to...like when you agreed to go to dinner.”

“Then Logan showed up,” Rory says grimly. 

“It might've been for the best that he did, but. It still hurt, even if it had no right to.”

“Why don’t you think you deserved to hurt?” Rory wonders aloud. “If you’re hurting, you’re hurting. You shouldn’t guilt yourself for it.”

“I’ve hurt you so many times, I figured it was comeuppance,” Jess admits. He sounds tired, Rory notes. Really tired.

“I get it. I’ve felt the same way.”

“I pushed aside the hurt, though, because after Logan drove up in his Porsche I started to realize that something was wrong. And after he basically mocked me--“

“Not basically, he did.”

He smiles in acknowledgement. “You weren’t the Rory I knew. And I knew you. I did. I guess when you only love one person...you know them better than you could possibly know someone else.”

(Is it possible he loves her more than any other man has? Rory’s starting to think so.)

“I left hoping that I’d opened your eyes to the problem, because I couldn’t fix it for you. I just hoped that whatever you chose after that...you were happy.”

“I was,” Rory assures him. “I went back to Yale almost

immediately, made up with my mom...everything was fixed. Except for Logan,” she adds with a wince. 

Jess nods grimly. “The next time I saw you…”

He’s bracing himself for the memory, she can tell.

“I didn’t think you would come. But you did, alone, and I hoped...I hoped. I got my hopes up once again. I was so happy, again, to see you, and it got the better of me. I know I should’ve asked explicitly if you were still with Logan--“

“No,” Rory interrupts firmly. “That’s not on you. I knew what you meant, and I as good as lied.”

Jess looks away for a moment. “Maybe.”

“But?”

“After I kissed you, and everything you said…” He exhales slowly. “That was the most it had hurt since that phone call three years before. 

“After that, I just kinda...shut that side of me off. I was never not in love with you, and I didn’t try to ignore that. I just didn’t let myself get my hopes up anymore. Every time I saw you after that, it was just a reminder of everything I regret.” He wipes at his eyes again. “I have so many regrets, Rory. There are a million things I could’ve done differently, and while I know that there’s no use dwelling on the past...sometimes that’s all there is to dwell on.

“I always felt like your love came with terms and conditions, that if I made the slightest mistake I could lose you. I…” He’s unable to go on. 

Rory reaches forward and wipes away a tear that's escaped his eye. “I understand. And I’m sorry, Jess, I am. I didn’t know…”

(I didn’t know that you were hurting so much.)

(He understands.)

“We’re here now,” Rory says, “and that’s what matters, right? You and me.”

The corners of Jess’ mouth quirk up. “Yeah. You and me.”

He squeezes her hand.

She squeezes back.

“It’s really late,” Jess says, glancing at the clock. “As much as I want to keep talking, you should go home and get some sleep. I know I need some.”

“You’re probably right,” Rory sighs. She stands up, and Jess follows suit. 

They meet in the middle of the room.

Jess takes her hand in his, and Rory places her hand on his shoulder. He leans down as she goes on her tiptoes; they meet in the middle again. 

His kiss is soft, and dare she say gentle; he cups the side of her face with his other hand as he kisses her. She’s melting into him, and she doesn’t want to let go, she wants him this close to her forever.

He pulls back -- she doesn’t want him to, and Jess doesn’t want to, either. “I’m going to ask you on a date now,” Jess murmurs, “officially.”

Rory grins. “Oh, yeah?” 

Jess beams in reply. “Yeah. So, I’m thinking...tomorrow night?”

“What time?”

“I’m trying so hard not to sound like a stereotype right now, and saying this goes against everything I stand for, but...I’ll pick you up at eight?”

Rory chuckles. “Right out of an 80s romcom.”

“Don’t I know it,” Jess agrees. “It’s only because I really should help out at the diner tomorrow -- as a thank you to Luke for letting me stay here, again -- and I will be closing up at 7:30 sharp.”

“It’s a date.”

“That it is.”

Jess leans in and kisses her again, before pulling back and smiling.

“Goodnight, Jess.”

“Wait-- before you go.” Jess goes over to the desk and opens a drawer, pulling something out and bringing it over to her. “These are the first six chapters of...whatever it is I’m writing,” he explains. “I want you to be the first to read them.”

Rory looks down at the manuscript and then back up at him, an awestruck look on her face. “Seriously?”

“Seriously.”

She takes it from him gingerly, and stares down at the title. 

_ Until The Tide Turns. _

Rory looks back up at him. “Thank you.” 

He grins. “Beat it.”

She grabs both sides of his collar and kisses him. “I love you. Unconditionally,” she whispers. 

He’s unable to reply; simply smiles at her, his eyes tender and soft. She lets go and turns to leave. 

“It was a swan.”

She looks over her shoulder at him, confused. “What?”

“It was a swan,” he repeats, “not a football. The black eye.” He points at his eye, as if she might have forgotten where it was.

She chuckles softly. “Thanks for telling me.”

“Anytime.”

“Goodnight, Jess.”

“Goodnight, Rory.”

The door clicks shut behind her. 

  
  


**Notes for the Chapter:**

> This might be messy I couldn't bring myself to finish editing it


	21. An Unforseen Rendezvous

**Summary for the Chapter:**

> The town is buzzing about Rory and Jess. They go on their first date in over thirteen years.

**Notes for the Chapter:**

> I'm so sorry it's been over two WEEKS since I updated - I got lazy and busy which is not a good combination but I digress. New chapter, please enjoy!

Rory sneaks back in through the front door, closing it slowly; she figures she’s gotten in and out without alerting her mother or Luke.

And she’s right - that is, until she walks into the family room.

It’s one in the morning, but the television is on, and Lorelai is sitting on the couch. Her back is turned, and Rory makes her way to her bedroom - it seems as though the television covered up the sound of the door opening and closing. However, a floorboard creaks under Rory’s foot, and Lorelai turns sharply at the sudden noise.

“Is this you making up for never sneaking out as a kid?” She asks wearily after realizing it’s not a robber, setting down her wine glass and placing a hand to her forehead dramatically. “Is this the day I suddenly have a rebellious teenager? ‘Cause I really don’t want to think about all the things you’ll have to make up for.”

“Think ‘Judd Nelson in Breakfast Club’ but take it higher,” Rory affirms. “And is it really sneaking out if I’m an adult?”

“You were the one tiptoeing inside like you were out with a boy,” Lorelai reminds her. Then she hesitates as if something has occurred to her. “Were you? Out with a boy?”

Rory rolls her eyes at Lorelai’s raised eyebrow. “Yes, I was with Jess. But we were just talking.”

“Mhm. ‘Talking.’”

“Use air quotes all you want-”

“Okay.”

“-but it’s the truth. I couldn’t sleep, so I walked over to the diner and...we talked.”

“So you said,” Lorelai observes. “So? Give mama the details. She needs a little break from _ Veep.” _

Rory sighs and sits down on the couch next to her mother, who turns off the television and faces her with an eager look on her face. Rory shakes her head in dismay. “It’s like living with Gossip Girl.”

“Hey, none of that,” Lorelai reprimands. “You kiss your ex-boyfriend for the first time in ten years, in the middle of Stars Hollow, for everyone to see, refuse to explain any of it, and now you come home at one in the morning after going to see him.” She lists all of these on her fingers. “Spill.”

Rory lets out a sigh. “I couldn’t sleep, okay? I was too excited and happy after everything with Jess that I...I just wanted to see him.”

“Aw,” Lorelai swoons, holding a hand to her heart. “That’s sweet.”

Rory shrugs, but she’s smiling all the same. “We needed to discuss...well, everything. He and I...we’ve been through a lot.”

Lorelai nods in understanding. “I get it. Communication is important, and something you two didn’t do a lot of back in the day.”

“Yeah.”

“And that’s all you did? Talk?”

Rory scowls. “Yeah!”

“Okay, just checking,” Lorelai says, holding her hands up. “But...is that going to happen? I mean, you said it might when you were dating him, and you two are older and the situation is different…”

“I dunno,” Rory mumbles. “We talked about the past, not the present, not really. Just that we’re gonna go on a date tomorrow night.”

(It feels weird saying ‘date.’ Like, she’s a thirty-two year old woman and she’s saying ‘date’ like...well, she doesn’t know what it’s like, but it still feels weird.)

“Ooh, what’re you gonna do?” Lorelai asks excitedly. “Mini-golfing? Snowman building? Bar hopping?” She gasps. “Oh! Are you finally pulling a _ Jerry Maguire _ like I suggested?”

“No, because I still don’t know what that means.” Rory bites her lip. “I don’t know. I guess we’ll figure it out then.”

Lorelai’s eyes widen as she purses her lips together. “The unpredictable Jess strikes again.”

“Mom.”

“Right, sorry. I like the kid, I do, I just want this to go better than it did the last time.”

“I do, too,” Rory assures her. “And it will. We’re both in it for the long haul. We’ve learned from our mistakes.”

“Good,” Lorelai says. “For what it’s worth, I really hope it works out.”

Rory’s a little taken aback; these are words she never thought she’d hear from her mother about Jess. “Thanks.”

Lorelai smiles warmly. “Now, go get some sleep, okay? It’s late.”

“Goes for you, too.”

“Of course. After this episode!”

Rory knows better than to argue that point.

**

Rory and her mother’s walk to the diner the next day might as well be a stroll down the red carpet, because everyone has their eyes on her. No doubt the entire town knows about her and Jess by now, and they’re definitely not trying to hide their knowledge. 

She spots Babette and Miss Patty peering through the diner window not-so-subtly, and they wave excitedly at her when she catches their eyes.

“Someone’s popular today,” Lorelai notes, pulling the diner door open, relishing in the chime of the bells. 

Rory snorts. “They haven’t been this invested in a relationship since you and Luke broke up.”

“Not even Peter interested them.”

“Paul,” Rory corrects, out of habit if not anything else, then cringes. “Good thing. They probably would’ve scared him or Logan away.”

“Well, it’s a good thing that Jess is experienced when it comes to dealing with Stars Hollow.”

Rory groans. “I just want one day of privacy. Not even a day, I’ll take a solid few hours.”

“Aw, my little celebrity,” Lorelai coos, wrapping an arm around Rory and squeezing her against her side endearingly.

Rory squirms and scowls. “Mhm. Fantastic.”

Lorelai claims an open table and sits down while Rory walks up to the counter. “Morning, Luke,” she says cheerfully, to which Luke gives a grunt.

“Your mother’s damn dog woke me up at 4:30 in the morning. Not something I particularly want to celebrate.”

“Aw, that just means he loves you.”

“He had to go to the bathroom.”

“Yeah, and he chose _ you.” _

Luke smiles slightly, amused, but he shakes it off. “The Saturday morning usual?”

“With extra toast,” Rory confirms.

She finishes paying when the curtain to the staircase is pulled back and Jess ambles into the diner, rubbing exhausting from his eyes. 

He sees her and freezes a little, a soft half-smile on his lips. Rory returns the gesture, with a smile that’s a little wider. Neither of them say anything; it’s a moment all too familiar.

Lorelai groans from somewhere behind Rory. “Damnit. It’s _ Rory and Jess: The Revival.” _

Luke grimaces. “Move it along, you two. I’ve got customers.”

(Rory’s the only one ordering, but she keeps that comment to herself.)

Jess appears to shake himself out of whatever reverie he’d fallen into. He approaches Rory; she can feel her heart speeding up in anticipation.

Before she can say anything, he sweeps her up in a kiss; slow, soft, sweet. In all honesty, a meteorite could obliterate the entirety of the diner, and Rory wouldn’t care, as long as he’s kissing her. 

Jess pulls back, both of them coming to the realization that there are about twenty sets of eyes ogling them. “Good morning,” Rory says cheerfully, a little breathless. 

He grins. “Mornin’.”

“Finally gave it a little somethin’, huh?” Babette calls, but Miss Patty shushes her.

“Let them have their moment,” she scolds.

“Oh. Sorry, darlin’, continue!”

Rory shakes her head and laughs. “They don’t have any boundaries, huh?”

“Not at all,” Jess concurs. 

“Guess we shouldn’t be surprised.”

Jess smiles guiltily. “I’d love to continue this, but I gotta go. I’m spending a few hours with Doula before I work at the diner, but I’ll see you tonight. Sorry I have to leave so soon,” he adds, a little reluctantly.

“No problem,” she promises. “I’ll see you tonight.”

He gives her a quick kiss and turns to leave.

“Hey.”

He stops and looks at her expectantly.

She moves closer to him so she can murmur in his ear, “wear that green t-shirt tonight.”

He smirks. “Noted.”

When the door shuts, Rory takes a seat at the table Lorelai picked out; her mother has a suggestive look on her face. 

When Rory notices, she rolls her eyes. “What?”

“My little baby’s in _ love,” _ she swoons.

“Love?” Babette exclaims. She turns to Patty excitedly. “They finally said it?”

“I told you, they said it at the festival.”

“Wow, you really can read lips.”

Rory groans and rests her head on the table top in frustration.

_ This is going to be a long day. _

**

Rory sits on the couch, reading her very worn copy of _ A Room of One’s Own _ \- she just finished rereading _ Ulysses, _ so she figured she might as well read Virginia Woolf’s response to it - and is dismayed when her focus is disturbed when the doorbell rings.

She’s not expecting Jess for another few hours, so of course that’s exactly who it turns out to be - he’s always been one to skip around the schedule. “It’s not eight,” is the first thing she says after she opens the door. 

Jess shrugs. “Luke told me to leave early, and I had nothing else to do, so I figured, why not start a little early?”

“Why did he let you stop working so early?”

“Apparently, I was a little too cheerful, and I was scaring off customers,” he admits, a little sheepish (or dare she say, flustered - a side of him she’s missed seeing). “But you know Luke. If I’m not getting into a fight or yelling at him, he thinks I’m downright chipper.”

Rory laughs. “Well, I’m glad, anyway. Means we have more time, right?”

“Exactly my thoughts,” Jess agrees. “And maybe Luke’s, now that I think about it…”

“Think he’s trying to set us up?”

“Playing matchmaker.”

“Matchmaker, matchmaker, make me a match,” Rory sings, turning around to grab her coat and bag from the hooks and front hall table. She’s still humming when she closes the front door behind her; Jess chuckles in amusement.

“So, where’re we going?” Rory asks; she notices his car is parked behind him in the driveway.

Jess shrugs. “I don’t have anything fancy planned. I do have a destination picked out, though.”

“How far?”

“Forty minutes, maybe?” He says. “I’ve never timed it.”

“Where are we going, then?” She asks as she slides into the passenger seat; he’s holding the door open for her.

He smirks as he gets into his seat. “It’s a surprise.”

“It’s not The Distillers, is it?”

He smiles in response. 

**

They drive around for a little while before they stop anywhere. 

Rory had missed this feeling - the windows cracked open a little, radio on or maybe a CD, the world passing by in a blur outside the car window, Jess by her side. They used to drive around a fair amount when they were together, especially when neither of them had any school, and it’s a pastime she’s very content to take up again.

Jess has the radio on, and _ All Out of Love _ is playing - Rory slapped his hand away when he tried to change the station when the song came on. “It’s sappy,” he complained, but she dismissed it with a wave of her hand. 

“It’s a classic. Now hush.”

_ I want you to come back and carry me home, away from this long lonely nights. I'm reaching for you, are you feeling it too? Does the feeling seem oh so right? _

Rory puts a hand to her heart. “He wants to be with the person he loves, but he just can’t bring himself to cross the distance.”  
Jess shakes his head. “It’s cheesy.”

“It’s _ romantic.” _

“And cheesy.”

Rory sings along for the rest of the song just to spite him.

_ Please love me or I'll be gone, I'll be gone _.

“Fine!”

He sings along, too. 

_ I’m all out of love, what am I without you? I can't be too late to say that I was so wrong. _

**

It’s been about forty minutes when Jess starts to look around for something or other; he ends up pulling over by a small, roadside diner that seems like it’s in the middle of nowhere.

“Here we are,” he announces once he’s parked; he unbuckles, and Rory follows suit. She glances through the window at the sign and smiles to herself.

Jess glances over at her. “What d’ya think?”

“I’m thinking I’m gonna like this date,” she says, stepping out of the car.

He chuckles and does the same.

**

Traveler Food and Books was a _ genius _ date idea, Rory decides. 

The hostess smiles when she sees Jess, immediately greeting him by name, and he asks her how her son is (Rory stares at him in astonishment), and soon, they’re seated at a table. 

She can’t stop looking around - there are shelves high on the wall, books facing the customers cover out; past the tables, there are rows of bookshelves, each packed full with books. “This is _ amazing,” _ she marvels. Jess chuckles under his breath.

“And _ you!” _ She exclaims in wonder. “How did you find this place? And how are you so chummy with everyone here?”

“I wouldn’t say _ chummy-“ _

“The waiter just asked how your book press is going,” Rory points out. “What happened to ‘I-don’t-do-the-small-talk’ thing? Are you suddenly a social butterfly or something?”

“Oh, _ god, _no,” Jess stresses. “I found this place years back, and just...kept coming whenever I was in Connecticut.”

“I can see why. It’s _ amazing _ here.”

“You’ve mentioned,” he comments humorously; she shoots him a playful glare. “It’s nice here. They don’t get a lot of traffic; it’s mainly regulars.”

“But how did you find it?” She asks, confused. “When?”

He shrugs, but he’s a little uncomfortable all of a sudden all the same. “I’d drive around a lot, that...that summer,” he explains somewhat awkwardly. “My first - or, well, only, summer in Stars Hollow. Had a lot of free time.”

“Oh.” She stares down at the table top for a moment. “Well, Stars Hollow has pretty boring summers.”

He snorts. “Understatement of the year.”

“I mean, the end of summer festival was fun.”

“If by _ fun _you mean insane, then yes.”

“I don’t know, the song was entertaining. You know, crazy hazy lazy days...”

“Aw, jeez, you’ve got it stuck in my head now.”

She can’t help but laugh. 

**

After they eat (a burger for Rory and a sandwich for Jess), and the bill is paid, they browse. They end up leaving with a big bag of books each.

“Should we buckle them in?” Rory wonders, starting at the two bags in the backseat.

Jess just laughs.

**

Rory pulls out a CD from his glove compartment - _ You Don’t Mess Around With Jim. _

“Jim Croce?” She asks in wonder. “Wouldn’t peg you as a fan.”

“Presumptuous of you.”

Rory clicks her tongue, nostalgic. “I haven’t listened to him in years.”

“Me neither,” Jess says. “Put it on. It’ll be nice to hear it again.”

They talk through the first half of the album, about Truncheon and Richard and their takes on new releases from the past few years, but fall silent when the intro to _ Operator [That’s Not The Way It Feels] _begins. 

_ ...Operator, well could you help me place this call? _

It’s a song she’s avoided for a while, ever since it came on the radio on one of her first days of Yale and she realized just how much it reminded her of Jess that she’d turned it off and hadn’t listened since.

_ I've overcome the blow, I've learned to take it well. I only wish my words could just convince myself that it just wasn't real, but that's not the way it feels. _

They’re almost through the second verse _ (There's something in my eyes, you know it happens every time I think about the love that I thought would save me...) _when Jess clears his throat and speaks. 

“Hits a little too close to home, don’t you think?”

Rory almost laughs, only for the fact that that was exactly what she had been thinking. “Maybe a little.”

“Can’t make an excuse about an operator, though,” he muses. “More of a ‘I should’ve spoken and then I didn’t’ situation.”

Rory sighs. “Maybe. But…”

“A tragic romance and all that, right?”

He’s looking over at her with a soft, nostalgic smile on his face, which she returns. “Your favorite.”

_ Operator, well let's forget about this call. There's no one there I really wanted to talk to... _

They’re both humming along when all of a sudden, Rory exclaims, “Pull over!”

Jess can feel his heart picking up, but he does as she says. “What is it?” He asks, his voice overwhelmed with concern.

She looks at him with wonder in her eyes. “I think the baby just kicked.”

“Wait, really?”

“Guess the kid likes Croce.”

Jess laughs in astonishment. He leans back in his chair; she likes this look on him, it’s very paternal. 

She invites him to feel, and when he does, he locks eyes with her - she finds herself feeling grateful that he’s here to share the moment with her. 

**

“I’m hungry.”

Jess laughs and looks over at her amusedly. “We just ate.”

“Hey, I’m a Gilmore. Fast-”

“-metabolism. Right.” He looks back out at the road. “We can grab some pizza?”

“Ooh, yes,” Rory agrees dreamily. “Pizza.”

They’re in luck - the pizza place in Stars Hollow is open. Jess orders a large cheese (Rory smiles to herself; he knows her so well) and they take it to the bridge, along with their large bags of books.

Jess pulls out one of the books he bought and begins to read it aloud. As Rory listens and eats her pizza, she thinks to herself: there is no place she’d rather be but here, with him. 

**

“I had a good time tonight.”

Jess looks over at her with a soft smile. “Yeah?”

“Yeah,” she affirms, a little breathlessly.

They make it to the diner, but Jess doesn’t open the door. He looks inside and then back at her, fiddling with his key. She lingers, not wanting to walk away and end the night. 

Thankfully, after glancing into the diner a second time, Jess speaks.

“Wanna come in for coffee and donuts?” 

Rory grins. “Definitely.”

He smiles and unlocks the door. He holds it open for her; as she walks past, she asks, “Won’t Luke be angry that we’re taking food from the diner?”

“I’ll reimburse him,” Jess shrugs. 

It’s good enough for her, Rory decides. He follows her inside and shuts the door behind her. She leans up against a table, waiting, but Jess doesn’t go behind the counter. He walks up to her with a soft little grin on his face. 

“Hey.”

“Hi,” Rory murmurs, straightening up. Jess cups her face in his hands and kisses her. It’s slow at first, but it turns urgent in no time at all; Jess wraps his arms around her waist and she wraps hers around his neck, clinging to him as he kisses her. They fall back a bit in the heat of the moment, so she’s leaning up against the table as he holds her against him.

They break away; Jess’ face is a little pink, which Rory finds endearing. She knows she must be flushed herself, and she tries to steady her breathing. There’s a look in his eyes as he gazes down at her that makes her want to skip the coffee and donuts and move onto something else entirely. 

She glances behind him towards the curtain where the stairs to the apartment before she looks back at him. She plays with the hair on the nape of his neck. “Do you maybe want to...to go upstairs?” She asks, trying to make it as casual as she can.

Jess frowns; he’s hesitating, not because he doesn’t want to, but out of caution. “You want to have the coffee and donuts up there?” He asks slowly, carefully. 

“Not really, but if you wanted to do...something else, that’d be okay,” Rory replies sheepishly.

“Rory…” He trails off warily.

“Look, we’re not rushing anything right?” She asks, biting her lip a bit. “It’s been a long time coming, don’t you think?”

The ghost of a smile lingers on his lips as he looks down at her. “Okay,” he murmurs, fiddling with the collar of her jacket.

He takes his hand in hers; he pulls back the curtain and they walk upstairs. 

  
  


**Notes for the Chapter:**

> ;)


	22. Romance and Records Rooms

**Summary for the Chapter:**

> Jess and Rory fall into a routine, but Rory still has some concerns.

**Notes for the Chapter:**

> First update of the last month of the year or smthin like that  
Some updates, I guess: I've been writing and brainstorming for other fics as well! Can't promise they'll be posted any time soon but

When Jess rolls off of her, Rory attempts to catch her breath. Yes, her heart rate has slowed to normal, but she’s only a moment away from jumping him again - _ rest is overrated, anyway. _

“What the hell was that, Jess?” She asks breathlessly. “That was…”

From somewhere to her right, Jess lets out a half laugh. Rory glances over at him; he has one arm behind his head and a satisfied look on his face. 

“Amazing?” He suggests. The corner of his mouth quirks up. 

She nods and swallows. “Yeah.”

He laughs again and rolls over to face her better, propping himself up on his elbow. There’s something breathtaking about the way the soft moonlight peeks through the blinds and illuminates his face, she notes. 

“Why the hell didn’t we do this sooner?” Rory wonders. “If I’d have known...well, I wouldn’t have wasted so much time.”

Jess shrugs; he absentmindedly traces her collarbone with his finger as he speaks. “The timing wasn’t right until now.”

“I know, I just feel like we wasted so much time. Sometimes, I...I regret that we never did.”

He smiles softly. “Maybe. But I’ve got you here now, so I’m not too upset about it anymore.” 

In response, Rory reaches up and cups his face, brushing her finger against his cheek.

“I love you,” Jess murmurs. 

Rory smiles. “I love you, too.”

The look on his face is so familiar, and yet, this all feels so new. New, yes, and exciting, without a doubt - as much as she liked seeing the green t-shirt on him, she equally enjoyed being able to take it off.

She leans up and kisses him with as much energy as she can - which, in all honesty, isn’t much after the last twenty or so minutes, but she takes it in stride. Jess rolls back on top of her, and Rory thinks to herself in that moment that there is no place she would rather be. 

**

When Rory wakes up the next morning, she’s disoriented for a moment - for all the times she and Jess had hung out (read: made out) in the apartment, she’d never spent the night. Jess has his arm wrapped around her and his head tucked in behind her neck. (She smiles to herself when she realizes his hand is on her stomach.) She has to admit, she likes this. She likes this a lot.

Somewhat reluctantly, Rory rolls over out of his arms to face him. As much as she’d love to lie like that with him forever, she’s hungry, and more importantly, she needs coffee. Once she moves, he starts to stir, slowly waking up.

“Good morning,” she says softly, to which he grumbles incoherently. She laughs. “Not a morning person, huh?”

(She’ll save her quips for later; she wants to appreciate the moment. She can’t believe she’s waited fifteen years to discover all these little quirks about him.)

Rory leans in and plants a quick kiss on his lips. “Does that help?”

Jess grunts again, slowly opening his eyes and adjusting to the sunlight coming in through the semi-open blinds. Rory laughs a little bit to herself as she watches him. 

“What time is it?” He asks, his voice heavy with sleep. 

“About ten.”

Jess groans. “Damnit.”

Rory frowns. “What?” 

“The diner opened at eight,” he explains. “I was supposed to help open in exchange for the _ very _ generous favor of getting off early, but...”

“Everyone is downstairs,” she finishes for him. “So if we both go downstairs…”

“They’ll know we spent the night together.” He sighs. “God, they won’t shut up about it for ages.”

“I need coffee,” Rory pouts.

“I know. But there’s no machine up here, so.”

“What should we do?”

Jess props himself up on his elbow as he thinks it over. “Okay, how about this? You go downstairs, and I’ll scale the wall.”

“No, they’ll connect the dots and figure it out,” Rory laments. 

“Do _ you _ want to scale the wall?”

Rory scrunches her nose in disgust. “I’d rather not plummet to my death after only one night with you, thank you very much.”

“It’s two stories up.”

She sticks her tongue out at him. 

He laughs. “Well, we can always stay up here all day...in bed…”

Rory laughs as he rolls over and starts kissing her neck. “As tempting as that is, I really need some coffee. And some food. Preferably a lot of it.”

“We can wait,” he replies against her neck.

She’s this close to giving in. “We need to refuel.”

“I’ve got a little energy left. Now, be quiet and enjoy. I’m doing some of my best work here.”

Rory strokes his hair absentmindedly. “And I have to talk to my mom…”

Jess groans and rolls off of her. “Instant mood killer. Instant.”

She chuckles. “Sorry.”

Jess lifts himself up with a grunt. “Okay. Guess we just have to face it, huh?”

“I guess so.”

Jess gets out of bed and starts getting dressed, but Rory stays behind for a moment. “Hey, Jess?”

“Hm?”

“Toss me one of your shirts, would you?”

He frowns in confusion as he buckles his belt. “Correct me if I’m wrong, but didn’t you wear clothes yesterday?”

“Yes, but-”

“You definitely did, because I distinctly remember taking them off of you.”

Rory blushes. “Hey, if everyone’s gonna figure it out anyway, I’m going to lean into the whole thing. I get to wear your shirt the morning after.”

“Fair enough.” He reaches into the dresser drawer where his clothes are and tosses her one of his sweaters. “This good enough?”

She pulls it over her head without a word and relishes in the soft fabric against her skin. “Okay. Now toss me my pants.”

**

Rory braces herself right before Jess pulls the curtain back, she knows the drill; wide eyes, jaws dropped, whispers starting after approximately 15.6 seconds; the standard reaction to something surprising. She expects it, but it still embarrases her. 

They step into the diner, and it all happens right on cue. About twenty pairs of eyes blink at them, taking in the situation: a slightly disheveled Jess, and Rory wearing a sweater that is definitely too big for her. Rory counts the seconds in her head until Miss Patty and Babette turn to each other to whisper excitedly. Luke freezes mid-transaction stares at the two of them with an expression that under any other circumstances would be hilarious. 

“You can run for it,” Jess whispers. “I’ll take the bullet.”

“Are you sure?”

He nudges her. “Go. I know you want to talk to your mom,” he adds, a kind smile on his face.

She kisses him on the cheek before turning and walking out the door quickly. Jess steels himself; he accepts a rag from Caesar with a nod. 

He starts wiping down the counter somewhat absentmindedly, trying to ignore the stares he is receiving. A part of him wants to burst out laughing at how ridiculous this whole thing is, but he keeps his laughter in check.

Luke clears his throat awkwardly. “Good, uh, good morning, Jess.” 

“Morning, Luke.” 

“So, you, uh..you had your, uh, your date, with Rory, and-”

Jess cuts him off. “You really don’t have to do...this.”

Luke lets out a deep breath of relief. “Oh, thank god.”

Jess chuckles under his breath and continues wiping the counter.

Luke clears his throat. “Jess?”

“Hm?”

“You know Lorelai is going to murder you, right?”

Jess dismisses this with a wave of his hand. “Maybe thirteen years ago. Rory’s an adult now; I’m not too worried.”

Luke nods once in understanding. He looks at his nephew thoughtfully for a moment. “You look happy.”

“I am,” Jess replies immediately, something he’s done a million times before. But he finds that this time, he actually means it. 

**

“I’m home!” Rory calls out, dragging her bag of books and her clothes from yesterday inside and closing the door behind her. 

“Be there a minute!” Lorelai yells back. One moment later, she hurries down the stairs, an excited look on her face. 

Rory laughs. “Pace yourself, okay?”

Her mother dismisses the advice. 

“Tell me _ everything,” _ Lorelai insists as the two of them take a seat on the couch. “It was your first date with Jess in over a decade. I need details.”

“Okay, well, first off, full disclosure,” Rory begins, feeling a little awkward, “I, uh, I kinda slept with him last night.”

“I kinda figured when you didn’t come home last night, but…”

Rory blushes. “Yeah, I just wanted to let you know before you heard it from...the rest of the town, as one might.”

Lorelai frowns. “Why would-”

“Well, we only woke up after ten, and the diner was open by then, so. It was either that or stay up in the apartment all day, and, well, I needed food - and coffee, of course - and to talk to you and - although, Jess _ did _ suggest tha-” She cuts herself off and turns pink.

To Rory’s relief, Lorelai pretends not to notice. “What, did you seduce him with all your rambling?”

“Oh, that’s how I get all the guys. Yeah, they can’t resist me tripping over my own tongue.”

“Alright, alright. Tell me about the date, though. What did you guys do?”

Rory then recounts the date, but she saves certain details for herself - like, when she showed Jess a copy of Howl and he just laughed and kissed her in response, or how he started writing in the margins of the books they bought the second they sat down on the bridge - she wants to hold onto them, just for a little while longer. 

But, in any case, when she’s done, her mother is satisfied. “I’m glad you had such a good time with him, babe.”

Rory blushes. “Thanks, mom. Really. It’s going to work this time around, me and him. I know it.” She means it, she does, but there’s still a nagging feeling she can’t quite dismiss. 

She’s still pulling her sleeves over her hands; Lorelai notices this and frowns. “Something else on your mind?”

Rory bites her lip. “I don’t...I don’t know. I just...I’m having a baby. How is Jess going to fit into that equation? Is he going to want to?”

“He knows you’re pregnant, and he’s still dating you, so I’d think so.”

“What if-“

“Hey, kid,” Lorelai interrupts, “you need to talk to _ him _ about this, okay? That’s the only way you can figure this out.”

“Yes, but-“

“No buts!”

Rory pouts. “I don’t want to ruin this.”

“You won’t,” her mother promises. She reaches over and squeezes her daughter’s hand. “You’re both in this for the long game, right?”

Rory nods.

“Then there’s nothing to worry about. It might be hard to figure out, it might not be; whatever it is, you two can handle it.”

“I guess you’re right.”

“Good.” Lorelai yawns a bit and stretches her arms over her head. “You want some coffee now?”

“Oh, yes, please. I didn’t get much sleep last night.”

Lorelai gasps. “Dirty!”

Rory laughs; this time, she doesn’t correct her. 

**

Over the course of the next week, Rory can feel things start to shift. On Thursday, she has an interview with the New York Times, and CBS calls on Tuesday - she prepared for both this time, and she feels safe saying that she killed it.

They’ve settled into a routine. Rory goes to the Gazette office to work - she needs to start working on the March issue, and the records room has a lot of articles and photos she can use for her book - and later she meets Jess at the diner and they go somewhere or other. They’re in what Lorelai has identified as their “honeymoon phase,” and Rory knows she’s right - she hasn’t spent a single night without him. 

Rory sits at her desk Friday afternoon, battling with MS-DOS - she’s almost figured it out, almost - and, quite honestly, she’s bored out of her skull. 

Thankfully, she’s saved from her boredom when Jess walks in with her lunch.

“Oh, thank you, thank you,” she gushes, accepting the bag from him gratefully, and immediately takes out the burger and starts eating. “I’d kiss you, but my mouth is full.”

Jess laughs. He takes a seat in the chair facing her desk, just like he did all those months ago, when he’d delivered her a book idea and essentially saved her from the rut she’d been in. “I appreciate you holding back.”

“So, what’s going on? How’s Doula?”

“Good,” Jess replies. “I’ve been wearing her down slowly - got her to read a book I bought her.”

“You’re insistent.”

“Learned from the best.”

Rory laughs and puts her half-eaten burger down. “Well, thank you, you’ve saved me from the mind-numbing boringness of this job. Sorry, Esther,” she adds, looking guilty over at her co-worker.

The woman shrugs, and casts a suspicious look towards Jess. “Mhm.”

Rory looks back at Jess, eyes wide in exasperation - “I saw that,” Esther reprimands - and sighs. 

Jess frowns. “Thought you were happy to be saving the Gazette and all that.”

Rory sighs. “I was. At first. But - and I love the Gazette, I do, I always have - I’m just...restless.” She glances behind her out the window for a moment. “I miss the passion that comes with a job I love, and not to mention the stability of a paycheck. I like having the ability to look through all the records for my book and all that whenever I want, but...I need to _ do _ something. Something I love.”

Jess nods in understanding and bites back an inappropriate comment - he’ll bring it up later. “I get it. I do. Maybe it’s time to...turn in the plaque,” he suggests, gesturing towards the _ Bernie Roundbottom _ name placard still sitting on her desk. “You’ve done good work for, what, six, seven months now? It’s okay if you want to quit.”

“Taylor would be mad.”

Jess scoffs. “When is he not?”

“Good point.” Rory stares at the computer and bites her lip. “I’m leaving eventually, I know, for whatever I end up doing. I haven’t heard back from anywhere yet, besides interviews, and there’s always Chilton - although, I can’t exactly get my master’s when I have a baby.”

“I’m always there,” Jess replies firmly. She thinks she knows what he means, but in all honesty, they haven’t discussed her pregnancy since they got back together. Sure, it’s been mentioned briefly - like when the question of protection came up, or when the baby kicked - but other than that? She guesses she’s been avoiding it. 

Rory makes a note to herself to bring it up later. She doesn’t want to derail this nice moment with a serious, scary chat about the future.

She steals a glance back up at him. The way he’s looking at her is so familiar by this point, and so is the feeling it invokes at her. At least now, she’s not afraid to do something about it. 

She stands up abruptly. “I want to show you something.”

Jess raises his eyebrows, but he gets up and follows her towards the records room nonetheless. 

When the door shuts behind him, the words “What did-“ are barely out of his mouth when she pounces, grabbing ahold of his collar and pressing her lips to his.

Jess responds almost immediately, and they stumble backwards, hands gripping and grasping almost desperately. He kisses her hard, open mouthed and sloppy as he backs her up against the shelves, Rory gripping his shoulders.

Before she knows it, Jess is lifting her up and pressing her against the shelves, the wood and metal pressing against her back. She wraps her legs around his waist tightly, grateful for how strong Jess has gotten over the years. 

In hindsight, hooking up in the records room of the Stars Hollow Gazette when really anyone at all, really, can walk in probably isn’t the best idea. But she’s probably about to quit, so, really, what’s the worst that can happen?

**

Rory was prepared for the worst, so it’s a surprise when Taylor grins broadly. 

“Well, that is good news, Rory, good news,” he declares. “We were all, of course, very grateful that you kept the Gazette going for the past several months. However, it’s time to turn a new page, don’t you think?”

“Sure,” Rory replies weakly. “So, this is my two weeks’ notice-“

Taylor cuts her off, a faux-guilty expression on his face. “Could we, uh, make it a little sooner?”

“What do you mean?”

“Well, the Spring Fling festival is coming up in a couple months, and we were hoping to, uh, include some _ additions _to it this year. The funds spent on the Gazette would be instead used for the festival, and, well…”

“I guess...the March issue is almost done, so-“

“Great!” Taylor cheers, cutting her off again in classic Taylor fashion. “Have that done by March first, would you? Thank you, Rory!”

He walks away before Rory can say anything along the lines of _ March first is tomorrow _ and _ the paper isn’t close to being finished yet. _Rory grimaces when she realizes how much work getting the paper out tomorrow entails.

Walking out of Doose’s, Rory reaches into her bag and pulls out her phone; it rings three times before Jess picks up.

“Jess, what are you doing tonight?”

He laughs. “I thought I had plans with you. Did you forget already? Remind me to buy you a pla-“

“No time for that!” Rory hisses. “I have to take a rain check - something came up.”

“Okay.”

She sighs. “Do you think you can help?”

“Well, I guess I’m free…”

“I have to finish the next issue of the Gazette by _ tomorrow, _and I’m recruiting. Do you think you can help?”

Jess hesitates. “Actually, I think I’m busy...“

“Ha ha, very funny. It’s all hands on deck! I have-“ she checks her watch- “Eight hours to get this done! Are you going to meet me at the Gazette or not?”

Jess blows out some air slowly. “Alright,” he concedes, “I’ll be there in a minute.”

“Thank you, thank you, thank you.”

Once they’ve hung out, Rory dials another number as fast as she can while hurrying towards the office. “Mom? I need your help with the Gazette. Again.”

**

Thankfully, they finish the issue with an hour to spare. Rory locks up as the copies print - they’ll distribute them later in the morning - and walks hand in hand with Jess to the diner. She’s wired, though, they both are, so neither of them can sleep.

Later, Rory sits in bed with a book as Jess shaves, waiting for him to finish up. The bathroom door closes and he climbs into bed next to her, grabbing his book and pencil from the nightstand. 

Rory glances over at him. Her worries from the day before have been on her mind since their shower, and she _ has _ to say something, she does, but the words are caught in her throat, she doesn’t understand how people talk about these things so easily- “Jess?” She says, a little too loudly.

“Hm?” 

She feels jittery, suddenly, anxious - is this the right time to bring this up? “Yesterday, when you said you were...that you’re always here, what did you mean?”

Jess looks up from his book and closes it. He doesn’t speak for a moment, just looks at her thoughtfully, and Rory wants to dive under the covers and hide. 

“I mean - we’ve never really - you know I’m pregnant, right?” She rambles nervously.

Jess chuckles. “I picked up the hints, yeah.” 

She watches him expectantly. 

“But...what I said before. I’m not going to be going anywhere anytime soon, Rory. You, me - this is it. You’re having a baby, and I’m your boyfriend, and I’m here for you. So - I’m always here. I’m assuming that’s okay with you.”

Rory blushes a bit; the anxiety is slowly fading away. “You mean it?”

Jess’ smile is kind. “I do.”

She feels a little bit better that night when she falls asleep in his arms. 

**

“I have to go back to Philly soon.”

Rory looks over at him, her toothbrush still in her mouth. “How soon?” She tries to ask, but it comes out unintelligible. She spits out the toothpaste and rinses before asking again, “How soon?”

He glances over amusedly. “A few days.”

“So, this’ll be, what, long distance then?” She asks nervously.

“Well, I’m not planning on breaking up, so.”

She smiles a bit. “Right.”

“For now, anyway,” he adds cryptically.

Rory raises her eyebrows. “What?”

“I haven’t told you yet, but…”

“What? What?”

“Truncheon is moving to New York. Greenwich Village, to be exact.”

“Jess, that’s great!”

He smiles sheepishly. “I guess.”

“No, it is! It’ll really get you guys on the map.”

“Maybe.”

“Maybe we’ll both end up in New York, then,” Rory says.

Jess grins. “Yeah, maybe.”

After a few moments, he speaks again. 

“Chris is actually getting married in a few weeks,” Jess adds, “and I was wondering if you’d, you know, be my date and all that.”

“Are you sure he’ll want me there?” 

He shrugs. “He’ll have to deal.”

“It’s his wedding!”

Jess chuckles. “He’ll be fine with it.”

“When’s the wedding?”

“Rehearsal dinner is two weeks from yesterday,” he explains, “and the wedding is two weeks from today.”

“I can meet you out there a couple days before the wedding,” she offers. 

“Sounds good to me.”

Rory smiles. “I want to meet Chris and Matthew,” she admits. “Seems like they’re really good friends.”

“They are,” Jess confirms. “If not two big pains in my ass.”

“They can’t be that bad.”

He laughs. “You’ll find out soon enough.”

**

Rory and Jess are sitting on the couch with his arm slung around her shoulders, watching _ Freaky Friday _ when Lorelai runs in.

“Hey, lovebirds!” She calls out. “Stop cuddling, it’s disgusting at a time like this. It’s an emergency, and you’re just sitting there, like it’s a normal day without an emergency!”

Jess glances behind him, his eyebrow raised skeptically. “What’s all this about?”

Lorelai holds up the phone. “Grandma just called. She says it’s high time we all get together,” she says to Rory. “You, me, Luke, and I quote: ‘Anyone else who isn’t that man you brought last winter with the bad car.’” Dramatic pause. “Who wants to take a road trip?”

  
  


**Notes for the Chapter:**

> Only eight chapters left...


	23. We Need To Talk About Emily

**Summary for the Chapter:**

> Jess, Rory, Luke, and Lorelai drive up to Nantucket to have a rocky dinner with Emily.

**Notes for the Chapter:**

> I actually despise editing but I finally made it through this so! New chapter time!

It’s a four hour drive to Nantucket (181.6 miles, Jess declares later), and at first thought, four hours may not seem that bad - but when the destination is considered, it couldn’t be any less appealing. Definitely considering _ who _ is attending. 

When Lorelai announces the trip, Jess tries to get out of going, but Rory won’t have it - “Oh, no, you don’t!” She exclaims when he tries to run out the front door after she looks over at him expectantly. Rory insists on driving up with him to make sure he doesn’t just ditch and drive straight to Philly. (He still tries, mostly joking, and it’s worth it even when Rory grabs the wheel and swerves and she swears her life flashes before her eyes.)

Jess decides to go back to Philadelphia the next morning, not that night, Rory wants him to stay the night (“There is no way she won’t let us stay the night,” Lorelai had pointed out. “Well, maybe not Jess. She’ll have him sleep in his car.”)

A four hour drive means lots of snacks, books, and road trip games that Rory plays and Jess makes snarky comments on as they drive up I-95. She reads _ In Our Time _ aloud to him, even though she still insists she hates Hemingway. _ (I’ll tell everyone in the world that you are the only one that matters.) _

He can’t stop glancing over at her amusedly, a little suspicious that this is all a dream and there is no way he’s finally hers again. It’s not an unfamiliar feeling. _ (Fall for them but don’t let them ruin you.) _

She catches the way he looks at her. _ (I’m going to stay with you. If you go to jail, we might as well both go.) _

It feels like home. 

**

Luke and Lorelai arrive first, but they wait for Jess and Rory to catch up before turning onto Emily’s street. Once they’re both parked, Jess and Rory clamber out of Jess’ car. Rory links her arm with Jess’ as they walk to the front door. 

“I could really use a cigarette right now,” Jess mutters in her ear.

She swats at him. “She’s not that bad.”

He simply scoffs in response.

Lorelai rings the doorbell, and Jess shifts awkwardly as they await the opening of the door. Berta opens the door, greeting them cheerfully, taking their coats and ushering them into the lounge. Rory steals a glance over at Jess and gives him a reassuring smile.

“Mom! We’re here!” Lorelai calls out.

Emily is sitting on the sofa with a novel in her hand. She closes it and smiles congenially. It falters a little when she sees Jess.

“Grandma, this place is really nice,” Rory gushes, hoping to divert at least _ some _ of her attention away from the unexpected visitor. Thankfully, Emily looks away from Jess and smiles at Rory.

“Thank you, Rory. It’s good to see...all of you.”

“Danger, danger,” Lorelai whispers loudly.

Rory doesn’t miss Emily’s eye roll. “This is Jess,” she says unnecessarily.

Emily’s expression doesn’t change. “I’m aware. What is he doing in my living room?”

“You said to bring anyone who wasn’t Kirk?” Silence. “I didn’t...I didn’t mention that I’m dating him?”

Emily smiles calmly, but there’s an edge to it, and a gleam of suspicion in her eye. “No, you did not. Hello, Jess.”

Jess nods. “Nice to see you again, Emily.”

Emily purses her lips. She looks from Jess to Rory to Lorelai to Luke to Jess again before recomposing herself. “Please, take a seat.”

_ “The Sun Also Rises. _ Nice,” Jess comments, gesturing towards the book Emily is holding as he sits down. Berta comes in and hands Lorelai and Luke some drinks before hurrying back to the other room.

Emily looks down at the book. “Oh, yes. Just a reread while I waited for you all to arrive.”

“Jess loves Hemingway,” Rory informs her.

Emily raises her eyebrows. “Really? I didn’t know you could read.”

Lorelai snorts mid-sip, choking on some water.

“Just learned how to, actually,” Jess deadpans. 

“How amusing.”

“You a Hemingway fan yourself?”

Emily frowns as if she’s surprised by the question. “Oh, I’ve read a few of his novels here and there. It was Richard who was the Hemingway addict, not me.”

Rory shifts a bit awkwardly at the uncomfortable silence that falls when Emily mentions Richard. She’s grateful when Jess pushes past it. “Rory was reading _ In Our Time _ aloud on our way up here, actually.”

“I take it you were the one driving?”

“What if I told you she’s just really good at reading and driving at the same time?”

To Rory’s surprise, Emily _ smiles _ at his comment. Lorelai looks over at Rory with a shocked expression, one that says something along the lines of _ can you believe she hasn’t kicked him out yet? _

“Do the rest of you want anything to drink?” Emily asks Jess and Rory. “Lorelai and Luke have been up here before, so Berta knows their drink orders. Rory, do you want a soda?”

Rory nods. “Yes, please.”

“And you, Jess?”

“Whiskey’s fine.”

“Very Lou Grant,” Rory whispers to him, repeating his words from last summer.

He glances over at her amusedly.

“So, Lorelai, tell me, how’s the inn doing?” Emily asks when everyone has their drinks.

Lorelai grins. “Oh, it’s great. People are coming from everywhere, really. Even Hemingway himself rose from the dead to have a look at our spa.”

“I don’t know why I asked.”

“It’s good,” Rory interjects. “Michel agreed to stay when Mom bought the expansion, so it’s as lively as ever.”

Emily nods in acknowledgement. “Oh, that french man. He’s very pleasant, isn’t he?”

Lorelai chokes on her drink again, which Emily frowns at. “Do I need to hire a drinking coach for you?”

Luke, who has been sitting there awkwardly the entire time, clears his throat. “I don’t know if _ pleasant _ is the right word, but he’s an institution.”

“You know, I’ve never actually met him,” Jess realizes. 

“Consider yourself warned,” Lorelai says, wagging her finger at him. “Few people have made it away from him without being in tears.”

“I don’t know, I think Jess could give him a run for his money,” Rory adds.

Jess raises his eyebrows in mock offense. “Am I really that mean?”

“Ask Lorelai,” Emily offers. “She’s always comparing me to Stalin, so I think she has a good idea of what’s _ mean _ and what isn’t. Or, so she likes to believe.”

Rory interjects before Lorelai can counter with a rebuttal of her own. “Grandma, I mentioned last month I was writing a book, didn’t I?”

“Oh, yes, you did,” Emily replies, her attitude changing suddenly. “It’s going well, isn’t it? I have an in with Simon & Schuster, if you ever need help getting a publisher. Oh, not that you would, with your talent, but there are many talented authors who just miss their cha-“

“Do you know _ the _ Simon? Or Schuster?” Lorelai jokes excitedly.

“I actually did date Richard Simon’s son for a while,” Emily replies cryptically.

Lorelai gapes at her until something dawns on her. “You’re joking, aren’t you?”

“Completely. I get to have some fun, don’t I?”

Jess looks very amused. “Maybe I should’ve stuck around for Friday night dinner that once,” he mutters to Rory. “I am _ very _ entertained.”

Rory swats at his arm, but she’s smiling nonetheless. 

“So, _ Jess,” _ Emily says, after Berta brings out more drinks, like she’s testing out how his name feels on her tongue. “What do you do?”

“My friends and I run a book press up in Philly.”

“A book press? That’s...interesting.”

Jess’ jaw ticks. “It’s not going to be making us the big bucks any time soon, but we like it.”   
Emily watches him, almost as if she is studying him, trying to get any information she can and then come out with her verdict. Right now, it’s a hung jury.

“Jess writes, too,” Rory adds hastily, trying to end the uneasy silence.

“Oh? Anything I would have heard about?”

“No,” Jess replies. Rory gives him a look. He sighs and continues. “I doubt it. Only one book out, and we only printed 500 copies back when it was published ten years ago.”

“It’s called _ The Subsect,” _Rory explains. “It’s really good.”

Jess smiles at her gratefully, but it fades as soon as he looks back at Emily. She’s still staring cryptically, and it’s driving Rory insane. 

“He’s writing another,” Rory blurts out. In retrospect, he may not have wanted her to announce it; however, Emily looks impressed - or, as impressed as Emily Gilmore _ can _ look. 

“What’s it about?” Lorelai asks. Luke, who’s been silent, frowns at Jess, discontent that his nephew didn’t tell him. 

“I’m afraid that’s top secret.” Jess takes a sip from his whiskey glass. “Truncheon’ll publish it when I’m done - that’s our press.”

“I suppose Rory will force a copy on me when it’s done,” Emily remarks.

“That is very possible.”

When Emily sort of smiles - in that classic Emily Gilmore way - and Rory really hopes that the jury is no longer out. 

**

In retrospect, it was naïve to think that the night would go by without conflict. It was going fine, really (the expression on Jess’ face when he saw the raisins in the salad was priceless), but this is the Gilmore family, afterall; respectful communication and smooth family dinners have never been something they were known for.

It starts to go downhill after a particularly witty story from Lorelai about a creepy family that visited the inn last month. Rory has noticed Emily’s constant glances over at her and Jess, and she’s not surprised when Emily’s gaze finally rests on them.

“So, Rory,” she begins, casually, but it’s still anything _ but _ casual, “tell me. What are your plans?”

“My plans?” Rory asks dumbly, feeling a little caught off guard.

“Yes, your plans. Are you staying with your mother in Stars Hollow? Are you moving somewhere else?”

Suddenly, the bottom of her glass of soda is much more interesting to stare at than her grandmother. “I, uh, I’m not sure yet,” she admits. “I’m waiting to hear back from some jobs, but-”

“Well, you _ must _ have a plan,” Emily insists incredulously. “You’re going to have a _ baby, _Rory, and it isn’t easy. You need a job with a steady paycheck, paid maternity leave - have you not done any preparations?”

“I submitted applications,” Rory replies, a little defensively. “I went to interviews. I made phone calls. I can’t rush the process.”

“It’s not about rushing, Rory, but you need to be persistent-”

“Mom, this isn’t like when you were young, eons ago,” Lorelai interrupts. “She can’t just walk in and ask for a job. It’s a long process, and there’s a lot of people applying, with only a few spaces-”

“I know that, Lorelai. All I’m saying is-”

“Let her breathe! She-”

They go back and forth, but Rory blocks it out, choosing to play with the edge of the table cloth instead. She can feel a bit of dread in her stomach growing and growing; she’s done all the preparation she can - or, well, she thought she did, but Emily is causing her only to be uncertain. And while she’s grateful for her mother’s defence, Lorelai’s words scare her, too. She knows the news industry is competitive, and jobs are decreasing, but what if she’s just not enough, and all the spots get filled? What if she was too late?

Jess places his hand on her thigh comfortingly. She wants it to help, but it doesn’t.

“Grandma,” she says, cutting off both her mother and her grandmother at once. “The New York Times said I’ll hear from them in a couple weeks at most, and CBS by the end of the month. I can’t do much more.”

Emily purses her lips. “I know, Rory, I do. I just want you to be okay, especially now that this _ hooligan-" _ has knocked you up-”

“Jess isn’t the dad,” Rory mumbles. 

Emily freezes. “He’s not?”

Jess shakes his head. 

“Then...then who?”  
The room falls silent. Emily looks from person to person, suddenly aware that there is a secret between the other four that she has yet to be filled in on. 

“Well?”

“You don’t have to say if you don’t want to,” Lorelai starts, but Rory shakes her head.

“It’s only fair.” She takes a deep breath in _ (one, two, three, four) _ and out _ (four, three, two, one). _ “It’s Logan.”

Emily blinks at her in shock. “Logan? Logan _ Huntzberger? _ Isn’t he married?”

“Engaged,” Rory mumbles. “He’s engaged.”

Emily stares at her, absolutely stunned, and Rory can only imagine what she is thinking. The prodigal daughter, making one grave mistake in the worst way possible, doing something no one would think her capable of. 

“Well,” Emily begins, her expression unreadable, “what’s done is done. I assume you’re not going to be with him, then? Raise this baby on your own?”

“Hey, I did it,” Lorelai objects. “And she can, too.”

“Yes, but she shouldn’t _ have _ to,” Emily says. “Her baby should grow up in a happy, whole family, including the father!”

“First of all, I’m with _ Jess,” _Rory snaps suddenly. “I’m not ditching the man I love just so my kid can grow up with a biological father that doesn’t even want anything to do with them! Second of all-”

“It’s not-”

_ “Second of all,” _ Rory says forcefully, “Logan has made it very clear he doesn’t want anything to do with raising this kid. He’s _ engaged, _ Grandma. This baby may be a repercussion, but it is _ not _ a regret, nor a mistake, and I don’t want you to act like I’m just clueless about it!”

“Then what’s _ his _ role going to be, then?” Emily counters, gesturing towards Jess. “He’s not the dad. Is he going to hang around your house all day, then drive back to Philly? Or is it all long distance? Is he moving to wherever you’ll be? And where will that be? Where are you going to live off of a paycheck you don’t have?”

Rory blinks a few times, trying to keep her tears at bay. She opens her mouth to speak, and she knows there are so many things she can say, Jess is moving to New York, she is too, he’s said he’s going to be there, but none of them come out. She pushes away from the table and hurries out of the room. A door slams down the hall.

The four remaining at the table sit there in stunned silence. Before Lorelai can start on Emily, Jess stands up as well. “If you’ll excuse me.”

He can hear Lorelai’s voice as he walks in the direction Rory did, but he tunes out the words. He goes to the room Rory dropped their things in and opens the door slowly.

Rory sits on the bed, crying, but she looks up when she hears him enter. She stops crying, sniffs, and wipes her eyes. Jess smiles kindly and closes the door behind him. He sits down on the edge of the bed, a gentle expression on his face.

“You okay?” He asks softly.

She shakes her head. “No. I don’t know. I just - I _ don’t _ know what I’m doing. She’s right, she is, but it was so much at once and I…”

Jess takes her hand in his and squeezes it. “I get it. I do,” he says, seeing her mouth open to object. “And you’re lucky. You have so many people who care about you and are going to help you figure it out.”

She brings her knees up to her chest and hugs them. “Jess, what are _ we _ going to do? I know you said you’re here for me, to help, but...what does that look like?”   
Jess hesitates for a moment. “What do you want it to look like? What do you need from me?”

“Jess,” she pleads. _ Please make it clear. _

He sighs. 

“Jess.”

He hesitates. “Let’s move in together.”

There’s a beat of silence as Rory processes his words.

“Are we ready for that?” Rory asks anxiously. “Is it too soon?”

“Not for me,” he replies firmly. “Not now.”

“Jess-”

“I’m ready for this,” Jess stresses, but he’s not trying to convince himself of it, not like last time. “I’m ready. To raise this kid with you.”

“Really?” She whispers. “Is it- is it what you want? I don’t want to...I don’t want you to feel like you have to - and what if you - I don’t want you to get involved in something you might not wa-“

“Rory.” She stops talking and looks at him. “This...you’re it for me. I want _ you _and...and anyone that comes along with you. I may not like these dinners that much, or going to big parties you might drag me to, or get along with all your family, or-“

Rory laughs. “Okay, okay.”

He smiles. “It may not be my kid, but…”

“As long as it’s what you want.”

“It’s what I want,” he assures her.

“Good. ‘Cause it’s what I want, too.”

He breaks out into a wide grin, the one that’s rare, but one that’s just so _ Jess. _“Yeah?”

“Yeah.”

“We’re gonna raise a kid together,” he murmurs. He sounds amazed, if not a little dazed.

“Yeah. We are.”

“If I’m being honest, those are the words I would _ least _expect us to ever say to each other.”

Rory stifles a laugh. “You have a point. But…” Her smile falters.

“What?”

“What about where we’re going to live? I have to get a job, too, and…”

“How about this?” Jess begins. “Give it a couple weeks before you start hearing back. We’re both moving to New York, anyway, so that’s not an issue. You’ll be coming to Philly for Chris’ wedding, and…”

“We can talk it all out then,” she concludes for him. “Okay. That sounds good.”

He nods. “Good.”

(He’s relaxed - it’s a very good look on him, she decides.)

“Do you want to go back to dinner?” He asks softly, brushing his thumb over the back of her hand.

She shakes her head. “I think I’m just gonna stay here.”

“Okay.” He leans in and kisses her head before standing up. “I’ll be back later.”

She smiles. “Thank you, Jess. I love you.”

“I love you, too.”

When Jess takes his seat at the table again, the tension is so thick he’s positive even a knife couldn’t cut it. Both Emily and Lorelai look defeated and angry; Luke shoots Jess a grateful look for his return. 

Jess clears his throat. He’s not usually a man of many words, at least away from the page, but there’s a little bit of anger directed towards Emily left in him and he has a few words he needs to say.

“Rory has a plan,” he says, surprising the rest of the table. “She may not have all the answers yet, but she’s done what she can so far, and the rest will follow through. She’s going to be okay, Emily, even if it’s not in the way you expected it to be. It’s okay if you’re disappointed, but it’s not okay to make her feel like what she has isn’t good enough. We’re going to raise her baby together, in New York, where I will work and she will, too. I may not be the biological father, but that doesn’t matter. What matters is that I’m here.”

Without another word, he begins to eat the rest of his meal, hoping that soon, he’ll believe his own words, too. 

**

He’s relieved that when later that night he’s reading in the lounge, he sees Emily knock on Rory’s door. He wonders if tonight was the right time to do this, to make all these decisions, to make a proclamation, but he pushes the thought away. This is what he wants, and what she wants, too; that should be the only thing that matters, right? Right?

(Somehow, he thinks there’s more to it than that.)

**

Separation is never easy, but it’s noticeably harder this time around. Twelve days isn’t enough, will never be enough, but somehow, fourteen is too many. 

“Two weeks,” Jess assures her. He pushes his duffel bag into the trunk and shuts it.

Rory watches his movements glumly. “I know. Still sucks, though.”

“Still sucks,” he affirms. 

“How’s it only been twelve days? Twelve days in a relationship and now we have to separate.”

“Think of it like seven months and twelve days but with a fourteen year break. Does that help?”

“Fine.” Rory crosses her arms across her chest and glances over at the car. “How long is the drive?”

“About eight hours.”

Rory scrunches up her face in disgust. “You gonna make it?”

Jess shrugs. “I’ve made longer drives than this.”

“Eight hours without reading? You might die.”

He chuckles. “I think I’ll survive.”

“You sure?”

“Might need a little incentive,” he suggests, moving a little closer.

Rory smiles, fiddling with the collar of his coat. “Yeah?”

“Yeah.”

She laughs before she leans in and kisses him. He sinks one hand into her hair, and part of Rory just wants to drag him back inside. 

They make out until Emily yells from the threshold, “You two are pushing it!”

They pull away; Jess is laughing a little bit. 

“Alright. Guess I better let you get in your car, then,” Rory sighs.

Jess nods. “Probably.”

Rory relents and lets go of his coat, but Jess leans in and gives her a quick kiss before opening his car door and climbing in.

“Two weeks.”

He grins. “Two weeks.”

Rory watches him drive away and out of sight, but admittedly, it’s not as hard as she expected, nor as painful as it has been in the past. Sure, she’d rather him stay right there with her, but this time, she knows he’s coming back. 

The future isn’t written in stone, but it’s close enough - she feels safe in saying that this time, it’s going to be good. Completely. 

  
  


**Notes for the Chapter:**

> Don't get all upset with the Jess stuff it's gonna be fine I promise


	24. Rory Disconnected

**Summary for the Chapter:**

> Jess arrives in Philadelphia, but they’re both already counting down the days.

**Notes for the Chapter:**

> this chapter is lame and basically just a filler, but i swear the next one will be much better!!

The drive back to Philadelphia is long, and by the time Jess passes the  _ Welcome to Philadelphia!  _ sign, the idea of going straight home and  _ crashing  _ on his bed is very appealing. But, he owes the guys a visit, among other things as well, so he drives to Truncheon instead.

Jess grabs his duffel from the trunk and walks up the steps of the brownstone. He checks, and sure enough, the door is unlocked. 

“Jeez, this place is a  _ mess,” _ he marvels, closing the front door behind him. Half-folded moving boxes are scattered around the room, cluttered piles of manuscripts and zines lay about, and neither Chris nor Mathew’s desk is visible under a thick layer of paper.

Matthew jumps, startled. “Yeah, well, you’re not exactly a neat freak either,” he retorts with a glare.

“How was your trip?” Chris asks pointedly. He shoots Matthew a look. 

Jess grins and drops his duffel by his desk. “It all worked out.”

“Oh, someone got some,” Matthew chortles.

“You’re cracked.”

“He just got back together with the girl he’s been pining over for  _ years,” _ Chris reminds Matthew. “I’d be concerned if he  _ wasn’t _ cheerful and happy. Or whatever the Jess equivalent to that is.”

Jess takes a seat at his desk. “We’re no Chris and Sara, however.”

Chris grins. “That you are not.”

“How’s Rory?” Matthew asks. “You two figure it all out, baby and all?”

Here Jess smiles a bit to himself, recalling his conversation with Rory the night before. “I’d say so.”

“We need more details. It’s been dry with John and Yoko over here.”

“Hey!” Chris objects. “Sara is  _ not  _ Yoko.”

“And you’re no John Lennon,” Jess adds; Chris scoffs in offense. “I was there for twelve days. What kind of hyper-detailed rundown do you want?”

“You just barely told us anything over the phone.”

“There’s a reason for that,” Jess replies. He reaches into his duffel and pulls out a notebook and a pen. “Wanted to save it for myself for a bit, I guess.”

“Well, honeymoon’s over, man,” Chris laughs. “Seriously. Everything’s...good with Rory?”

Despite his better judgement, Jess smiles. “It’s great.”

Matthew gestures for him to elaborate. 

“Look, I was just in Stars Hollow for a little, okay? Visited some old date spots, some new ones. Nantucket was interesting, but everything between us is worked out. That satisfy you?”

“I guess,” Matthew relents. 

“Thank you.” Jess leans back in his chair and crosses one leg over the other. He opens his notebook and clicks open his pen. After a moment, he stops writing, something dawning on him. “Wait. There’s one more thing.”

Matthew frowns in concern. “Yeah?”

“When Rory and I...figured it all out,” Jess says, “we decided that. That we’re going to move in together. In New York.” He glances out the window for a moment and then looks back at his friends. “And we’re going to raise her baby. Together.”

He waits for the words to sink in. 

Chris grins; he rolls over in his chair and claps Jess on the shoulder. “Good, man, this is good. I’m happy for you.”

“You stole my line,” Matthew jokes, but he can’t summon any malice. “This is great, Jess, really.”

Jess can’t help but smile a bit to himself. Who would’ve thought? “Yeah, well…”

“What about the ex? The blonde dick?” Chris asks suddenly. “What’s his role in all this?”

“Didn’t want one. He’s in London, has a fiancé. He’s not going to be in the picture.”

Chris nods in acknowledgement. An awkward since slowly creeps over the three. 

Jess goes back to his notebook and continues scribbling down his thoughts, a focused look on his face. 

“What’re you writing?” Matthew asks non-committedly, turning around to get back to his computer. 

“Nothing coherent.”

“He’s got a lot of creativity now that he’s got his  _ muse  _ back,” Chris intones in Matthew’s direction. 

Jess scoffs. “Oh, please.”

“Not denying it?”

“I’m not,” Jess admits after a moment’s worth of hesitation. 

“New idea?”

“Yeah.”

“New York Times Bestseller list, get ready,” Matthew adds, still looking at his computer. 

Jess shakes his head and keeps writing. “How’s the wedding planning going?” He asks Chris. “Still needlessly bickering?”

“Ah, but that’s how you know it’s love,” Chris muses. “It’s been good. Hit a bump in the road when her mother came to visit, though.”

“Oh, God. What did Sara do to poor Lorraine?”

“Shut up.  _ Lorraine  _ was being her usual critical self. The bridesmaids dresses are too short, why a March wedding, why are we getting married at a public rec center-“

“Can’t believe Sara didn’t flip her lid.”

Chris snorts. “She almost did. But thankfully, Matthew was able to  _ distract _ her mother.”

“Gross.”

“Not like that!” Matthew objects. “I just gave her a tour of Truncheon. A very thorough one, might I add. Came up with some stuff you wouldn’t believe. She might think it’s haunted now,” he adds as an afterthought.

Jess snorts. “Not a bad consequence.”

“All’s well in the wedding department,” Chris concludes. “You’re bringing Rory, I take it?”

Jess nods. “She’ll come up a couple days before.”

“We’ve never actually met Rory, have we?” Matthew wonders. “We  _ saw  _ her, what, eleven years ago at the open house? But that’s it.”

“And you’re going to be  _ nice,” _ Jess says firmly, mostly directed towards Matthew.

Matthew holds his hands up in surrender. “I’ll do my best.” He catches Jess’ expression. “I‘ll be nice.”

“Goes for the both of you,” Jess reminds them. He leans back and continues to write, scribbling word after word down in his notebook. 

“You think Sara and Rory will get along?” Chris wonders.

“Don’t girls usually?” Matthew asks distractedly.

Jess snorts. “Sure, Matthew.”

“Okay, now, everyone, shut up. I have to read  _ George’s  _ manuscript.”

“Lincoln or Walker?”

“Porter.”

“Oof. Good luck with that one.”

Matthew grimaces and salutes mockingly. 

As much as he loved being in Stars Hollow for the past couple weeks, Jess has to admit, it’s nice, being back in Philly, with his friends and his work and everything that has been his home for the past eleven or so years. They only have so much time until they move, anyway. He’ll miss it, definitely, but he’s also excited - returning to New York with Rory is something like a dream come true.

**

“What’s all this?” Lorelai asks, wading through Rory’s clutter warily. “Are you planning on paper maché-ing something later, or…?”

“Cleaning through things,” Rory replies distractedly. “Hand me that list, will you?”

Lorelai confusedly hands Rory the piece of paper on her bed that she was pointing to. “Seriously, mommy needs answers, or she’s calling the Merry Pranksters to pick you up.”

Rory looks up at her mother. She’s sitting cross legged on the floor of her room, surrounded by old copies of  _ The Franklin _ and  _ Yale Daily News,  _ magazines, notebooks - anything made of paper. “Sorting. I’m moving to New York in a month or two. I’m not living out of boxes this time.”

“Right. The big move.” Lorelai nudges Rory with her foot. “Hey, kiddo, take a time out for a second, okay?”

“Just for a second, cause that’s all the time I have.”

“Hey, Monica, you’ve got two months. Chill.”

“A  _ Friends  _ reference? I thought you said that was beneath you.”

“Yeah, well, the well’s run dry,” Lorelai replies dryly. “C’mon, get out of this mess for a bit.”

Reluctantly, Rory stands up and follows her mother out of her bedroom and into the kitchen. Admittedly, it’s nice to get out of the clutter and breathe. 

Lorelai takes a seat and gestures for Rory to do the same. “Okay, so, what’s with the sudden interest in decluttering? Did Marie Kondo get to you?”

Rory snorts. “I want to be prepared,” she says stubbornly. “This move is going to be pretty permanent. I need all my stuff organized so when it comes time packing will be easy.”

“Yeah, but organizing all your own newspapers? I mean, this is all bordering on obsessive.”

“There’s nothing wrong with organizing all my newspapers.”

“Is something on your mind?” Lorelai inquires. “Like...a certain guy or fetus or…?”

Rory sighs. “Look. I’m just waiting to hear back from the places I’ve applied to - ABC and NBC passed - and  _ somebody _ confiscated my tap shoes, so I have to get my stress out somehow. And while Jess sending me updates on stupid things his friends said is entertaining, it’s not really an outlet, so.”

“Buck up, kiddo,” Lorelai says sympathetically. “You’ll get those acceptance emails soon enough. And just out of curiosity, what kind of stupid things?” She adds as an afterthought.

“I believe my personal favorite was, and I quote, ‘it’s times like these that I regret voting for  _ John Berry _ in the 2004 election.’”

“Which one said that?”

“Matthew.”

Lorelai snorts. “Good to hear that’s the kind of company Jess is hanging out with. No offense, but he can be a little too...pessimistic.”

“You’re absolutely right. And yet, it’s endearing, isn’t it?”

“Debatable.” Lorelai pauses. “How is the hoodlum, anyway?”

Rory groans. “Would you stop calling him that?”

“Never. I may get along with him now, even be  _ friends, _ but he’s always going to be a hoodlum to me.”

“Whatever. He’s good, though. I think he’s happy to be back in Philly for now.”

Lorelai nods. “And he’s okay with everything? The move, all that?”

“Yep,” Rory affirms. “We’re going to start looking at apartments online when I go up to Philly, and then move on from there.”

Lorelai taps her fingers against the counter absentmindedly. “Good.”

Rory frowns. “Something else on your mind, mom?”

“Oh, nothing, really, just…” She catches Rory’s gaze. “I guess I just never imagined all of this happening, you know? Not that I don’t like it,” she adds quickly, “it’s just a lot to adjust to in a short time. And you’re going to be moving out for good so soon…”

“This feels right,” Rory assures her. “Yeah, is it what I expected? Not really, but life’s been screaming at me that that is often the case, so I’ve learned to take a hint.” She cracks a smile. “Besides, we have a  _ lot _ of movie watching and all that to do before I go, so don’t get bummed out yet!”

Lorelai manages a smile. “Yeah. You’re right. I’m gonna miss you, though, kid.”

“I’ll miss you too. But I’ve moved out before, and we’ll move through it like we always do. And I’ll be in good hands, I promise.”

“Good hands?” Lorelai asks suggestively.

“Shut  _ up.” _

**

For the next two weeks, Rory misses Jess, of  _ course  _ she does, but it’s different than other things she’s missed before. It’s not burning, it’s not cold, it’s not  _ painful,  _ not when she knows he’s coming back - there’s just an  _ absence,  _ a noticeable one, and his texts don’t seem to fill that empty space.

The day before she drives up to Philadelphia, Rory crosses off the previous day on her calendar and takes a look at all the boxes she’s brought to her bedroom and started to fill. This impending change is a big one, maybe just a little terrifying, but. But the thing is, she’s ready. She’s  _ ready _ for a life with Jess, this  _ love  _ with

him, this inevitable love that she’s been on the road to ever since she first met him that one October night. 

Jess hurt her before, but he’s more than made up for it since, and Rory knows that he was right. This - this is it.

It’s it for them, and that’s good, really good, something she thinks she’s wanted for a long time. It took a lot to rebuild this, rebuild  _ them,  _ lots of work, but it was  _ good  _ work. And now that the final pieces have been glued together, it just feels right. 

**Notes for the Chapter:**

> six chapters left...


	25. A Philadelphia Love Story

**Summary for the Chapter:**

> Rory joins Jess in Philadelphia for Chris and Sara's wedding.

**Notes for the Chapter:**

> Sorry for the long wait! I had a family emergency last month that took up a lot of time and energy, but fortunately, I am back with an admittedly long and self-indulgent chapter. Enjoy!

The two weeks move by slowly, but finally, _ finally, _ the day Rory leaves for Philadelphia arrives. She packs her suitcase, kisses her mother and Luke on the cheek, and gets in the Jeep. (She won’t need a car in New York, so what’s the point in getting her own? She’ll make it a couple months without a car; thankfully, Lorelai has no qualms with lending her the Jeep.)

She puts on _ Deja Vu _ on the way there, _ play your love songs all night long for me, only for me, _ and she thinks about Jess, and the home _ they _ are about to build. (A cheesy thought, she knows, but as a journalist, she has to call it like she sees it). It’s three hours - _ our house is a very very very fine house - _ and twenty-six minutes until she gets to Philly, gets to see _ him _ again. Twelve days wasn’t nearly enough to take him in, to memorize his every detail, to make up for the last thirteen years without him. Three hours and twenty-six minutes. 

She parks outside his apartment building; it’s a nice brick building with a couple trees outside. It all feels very Philadelphia-esque as she uses the key he gave to her before he left to get inside. He lives on the fourth floor, and of course there’s no elevator (not even a dumbwaiter for her to sneak into) so she struggles up the flights of stairs, all the whole wondering if this is one of the ways he got in such good shape. (Probably. She takes her sweet time up the stairs, but she’s still convinced her heart is about to explode when she makes it to his floor.)

She finds his apartment quickly - number 407 - and knocks on the door. She knows she could use the key, yes, but there’s some odd thrill she gets that she cannot explain when the door opens and she sees him. Rory immediately grabs him by the collar and pulls him in for a kiss, hungrily, passionately, relishing in his response. It’s brief, however; Jess pulls away quickly, a little breathless, smiling sheepishly. “Rory,” he says, gesturing behind him, “meet my friends. Chris, Matthew, and Sara.”

Rory turns pink in embarrassment and waves slightly. (She’s suddenly very grateful she didn’t reach for his fly like she’d considered.) Jess is looking at her rather amusedly - she makes a mental note to reprimand him for it later. “Sorry,” she mumbles. 

The girl - presumably Sara - smiles and waves back. “Don’t worry about it. There was this one time where Chris and I-”

“Hey, I thought we decided we would _ never _ bring that up again,” one of Jess’ friends - Chris, Rory assumes - objects. 

“No, _ you _ decided,” Sara retorts. “I still intend to bring it up at every social gathering because it is a crowd _ pleaser.” _

“Although I don’t think the rabbi will appreciate a, how you say...tasteless story at the wedding,” the other friend, Matthew, adds. “But, for the record, I _ love _ it. If that does anything to end this argument for the thousandth time.”

“See?” Sara exclaims. 

Chris glares at them. “You’re working my last nerve, the both of you.”

“Just like y-”

Jess shoots them all a warning glance before turning back to Rory. “These are my friends,” he says somewhat apologetically. “Chris, Matthew, and Sara. She’s Chris’ fiance.” He points to each of them respectively. “Don’t mind them.”

Matthew looks at Rory skeptically. “You’re the girlfriend, then?”

“I’m Rory, yeah,” she confirms awkwardly. When Matthew doesn’t stop looking at her strangely, Jess swats at him.

“Take a seat,” Jess tells her. “You want some coffee?”

“Yes, please. It’s been four hours since I’ve had any. I thought I would die.” 

He shakes his head amusedly. “I’m right on it.”

Jess busies himself with the coffee machine while Rory takes a seat on the leather couch next to Sara. She’s freckled with wavy red hair and brown eyes, and wears slacks and a button up. “This is good timing, actually,” she informs their new arrival. “We need your opinion on something. We’re trying to decide what order to put our names on the thank you cards. I say ‘Sara and Chris-‘”

“‘Chris and Sara’ is _ objectively _ better,” Chris cuts in. 

Sara elbows him. “_ Anyway, _ that’s what we’re trying to figure out.”

“Just go with what you had on the invitations,” Jess calls over from the kitchen. “And then be done with this idiotic argument.”

“The invitations weren’t the same,” Chris argues. “We did it alphabetically.”

“Then we should put my name first this time!”

“But _ Sara and Chris _ just doesn’t _ feel _ right. Like saying ‘dad and mom’ instead of ‘mom and dad.’”

“Or Jack and Jill,“ Matthew offers.

“Trials and tribulations,” Rory offers.

“War and peace.”

“Law and order.”

“Front and center.”

“Fish and chips.”

“Bed and breakfast.”

“Coffee and donuts.”

“Ranting and raving,” Jess says pointedly. He brings Rory her coffee, and she accepts it gratefully.

“Thank you, thank you. I love you,” she gushes.

“Love you, too,” he replies, so easy, and sinks down in one of his chairs. 

“So, what do you think?” Sara asks eagerly. 

Rory laughs. “I’m sorry, Sara, but I’m going to have to go with ‘Chris and Sara.’”

“Traitor!” Sara exclaims jokingly. “I thought we had something, Rory.”

“I didn’t want it to end like this, but…”

Jess’ phone begins to ring. He picks it up, brow furrowed. “What? Luke, calm down, what is it?” He gives Rory and his friends an apologetic look before getting up and going out into the hall. “Well, tell Kirk to shut up, then. You do that even when he’s not doing anything.”

He closes the door behind him. Rory gets a good look around the studio apartment; there are records framed on the dark walls, all the furniture is dark oak, and there are books on every surface. She makes a mental note to ask him about the records and book jackets he has hanging in frames. 

It’s all very Jess, she decides.

“So, Rory,” Sara says earnestly, “how’d you and Jess meet?”

Rory laughs. “Now, _ that’s _a long story.” She catches Matthew giving her a look and fidgets uncomfortably. (Chris notices and elbows Matthew in the ribs.) 

“God, I’ve known him, what, fifteen years since last October? We dated my senior year of high school, but...life got in the way, you know? We only just got back together last month.”

“Tragical romance and all that, right?” Chris muses.

“I suppose so.”

The door opens and a slightly hassled Jess walks in. “Luke was roughly five seconds away from murdering Kirk, but I think I talked him down.”

“What was Kirk doing this time?” Rory asks.

“I couldn’t tell - you know how Luke gets when he’s angry. I think it has to do with _ Clue _ \- the movie - but I’m not sure.”

Rory snorts at the bewildered looks on all of his friends’ faces. Jess, amused as well, sits back down in his chair. 

“Are you excited for the wedding?” 

Chris grins at Rory’s question. “Are you kidding? We’ve been counting down the days for months.”

Rory smiles. “Aw, that’s sweet.”

Sara scowls. “My mother’s going to be a _ nightmare. _ Can’t wait for everything to be _ done.” _

Jess snorts. “That’s considerably less sweet.”

“I’ll take it in stride,” Chris says, wrapping his arm around Sara and bringing her close. “After all this, we’ll be married. I think that makes Lorraine spending an hour asking why we don’t have a _ priest _ worth it.”

Sara smiles. She leans in and kisses him, hand on his chest. It’s sweet, but then Jess breaks the moment by coughing.

Chris shoots him a look. “Way to ruin the moment.”

“Hey, we’re all here as a group. Make out on your own time.”

“Hey, we all know the second we all leave you and Rory are going to be all over each other,” Matthew points out. 

“This is _ my _ apartment.”

As Jess and Matthew bicker, Chris checks his watch. “We should probably order the food soon if we want to give the, uh, reunited couple adequate time alone.”

“Is Chinese okay?” Sara asks Rory. “There’s this place only a few blocks from here - really good food, but the guy that delivers the menus is kind of a jerk.”

Rory nods. “Fine by me. It’s one of the three best kinds of takeout, objectively. Indian, Chinese, and pizza.” She counts them off on her fingers. 

“Couldn’t have said it better myself. I knew you were a kindred spirit.”

“_ Kind of a jerk?” _ Matthew asks incredulously, only now tuning in. “He’s diabolical.”

“Matthew has a theory that he’s been leaving one menu more at his apartment each time,” Jess explains. 

“I think he’s onto something,” Chris interjects.

“Thank you!”

Jess shakes his head. “You’re both cracked.”

Chris grins. “That’s what makes us so fun.”

(Rory can’t help but agree.)

**

Jess orders the food, and it arrives fairly quickly; Jess tips the delivery guy, then sets the food down on the coffee table. Chris and Matthew excitedly dive for it, tearing open the bag and sorting through the many boxes and bags of egg rolls. 

(As they eat, Sara warns everyone about one of her bridesmaids, Clara, who has a thing for Jess. “She’s not very forward, but she’ll be staring. A lot. Wear a tan suit if you want to drive her away.” Rory laughs at the disgusted look on his face.)

Once everyone is done eating, Jess starts to hurry his friends out. Matthew objects and Chris makes a slightly crude quip - which Sara apologizes to Jess for - and eventually, all three of them are out the door.

Jess starts cleaning up the takeout, throwing out the empty boxes and putting leftovers in the fridge, along with Rory’s help. 

“What’d you think?” He asks once they’ve cleaned it up; nonchalantly, but she can tell he cares.

“They’re all characters, that’s for sure.”

“No kidding.”

“But I like them,” Rory declares. 

Jess starts to smile. “Yeah?”

“Yeah.”

“I’m glad.”

“Although...what was Matthew’s problem with me?” She asks, wrapping her arms around herself. Jess softens a bit.

“Don’t worry about him,” he assures her. “He’s just...overprotective. They both are, but Matthew...there were a few too many nights of me pining and grieving that he’s struggling a bit to give you another chance.”

Rory stares down at her feet. “Right.”

“But,” Jess adds leisurely, “just give him time. He’s a good friend, just like Chris, and you’ll grow on him eventually.”  
“Like a fungus,” Rory adds glumly. 

Jess snorts. “C’mon, there’s more to all this than _ that, _ Gilmore. You’re smart, you’re _ gorgeous, _ and-”

“Just to be clear, I wasn’t fishing for compliments,” Rory interjects, blushing. “But if you wanted to continue, that’d be fine by me.”

“You’re _ gorgeous, _ witty, and have had the _ best _ comeback since Michael Jordan decided to go back to basketball. And, might I add, the sexiest rambler I’ve ever met. Matthew will come around eventually once he gets to know you.”

Rory smiles. She sets her hands on his shoulders and kisses him softly. She moves to pull back, but he snakes an arm around her waist, holding her close as he kisses her a little harder.

“Mm - Jess,” she says between kisses. “One sec.”

He pulls back and takes his arm back, watching her curiously. Not breaking eye contact, Rory grabs the hem of her shirt and pulls it over her head, letting it drop to the floor.

Jess chuckles under his breath. “You trying to tempt me?”

“I might be,” Rory says innocently. He watches her intently, a heated look in his eyes as she kicks her shoes off and pulls off her hair tie, her hair falling loose around her shoulders. 

He takes her by surprise when he suddenly wraps an arm around her and pulls her to him, tangling his other hand in her hair. She kisses back, and he groans slightly against her mouth, sending chills down her back.

They stumble towards his bed. She falls back on it, Jess on top of her; he kisses her mouth, jaw, neck, anywhere he can reach with her arms wrapped tightly around his shoulders. 

“So what exactly was Luke freaking out about?” She asks absentmindedly, gasping a bit when he sucks hard on her neck in that one particular spot by her ear that always drives her crazy.

“Kirk was trying to sublet the diner for a murder mystery party, I think. Watched _ Clue _ and had an epiphany.”

She struggles to focus as he drags his hands down her body. “So what was-” 

Jess lifts his mouth from her neck and looks at her amusedly. “Do you really want to spend our _ alone time _ discussing Kirk?”

“Not especially.”

“That’s what I thought.”

“We can save it for later. I’m gonna need more deta-”

“All due respect, Ror,” Jess laughs, “but shut up.”

She raises an eyebrow. “You’re gonna have to find a better use for-”

His lips are back on hers before she can even finish her sentence.

**

The rehearsal dinner starts at 7pm the next day. While Rory insists on them leaving an hour early (which means showering at 4:30 and getting ready at five), it still gives them plenty of time to sleep in. Jess, ever consistent, refuses to get out of bed until eleven, and even then he’s grumbling and exhausted until Rory forces coffee upon him. He makes them a late breakfast and they read together for the next few hours.

“I’m driving,” she announces, grabbing the keys after they’ve both gotten ready.

“Don’t kill my car.”

“We’ll see how it goes. I have a bad track record with wildlife.”

Jess looks at her confusedly, following her out of the apartment.

**

“If you were going any slower, we’d be going backwards,” Jess laughs, eyeing her amusedly from the passenger’s seat.

Rory sticks her tongue out at him. “I still don’t like driving in big cities.”

“I can see that. I just don’t get how you haven’t adapted after years of travelling from big city to big city. How did you get around New York or Chicago?”

“I took a taxi when I needed to get somewhere.”

“Ah.”

“Besides,” Rory continues, “no one in Philadelphia knows how to drive. I think I saw a guy driving in the bike lane.”

“Very possible. To be fair, I’m sure that happens in New York, too.”

“Well, you’re the native, not me, so.”

Jess grins. “We’ll be there soon enough.”

“We have to find an apartment,” Rory reminds him.

“We can look online tomorrow.”

“In a good school district.”

“Right.”

“And-”

Jess starts laughing. “Ror, it’s okay. We’ve got time.”

“I know. I just…”

“It’s okay to be worried. But we’ve got it under control, right?”

She reaches over and squeezes his hand. “Yeah. We do.” She shoots him a smile before taking her hand back and looking back at the road.

“Have you heard from Logan recently?” Jess asks out of the blue. 

Rory frowns at him, surprised. “Logan? No, why?”

“Just wondering. Figured the guy would be checking in.”

“He hasn’t yet, but I’m sure he will eventually. It’s his kid too, right?”

Jess nods; something in his jaw tightens despite. “It sure is.”  
Rory catches bitterness in his tone, “Jess. You know Logan’s going to be in my life, in our kid’s life. We’ve talked about this.”

“Have we, though?” Jess sighs. “Look, Ror, I know that being with you means that there are a lot of people that are going to be in my life from now on, but how much is _ he _ going to be involved?”

“I assume he’ll visit or invite him or her over to stay. My dad used to do the same.”

“Right.”

“Jess.”

“No, I get it, I do. He’s gonna be in your life and therefore mine. And while we’re on the subject, have you even told him we’re together yet?”

“...Not yet,” Rory admits guiltily.

“Okay.”

“Jess.”

“I get it.”

Rory grips the steering wheel a little tighter. “Jess, this is exactly why it didn’t work out the last time. You need to talk to me about these things.”

“I know.” Jess takes a deep breath. “I just...I want to have a good time tonight, and tomorrow, at the wedding. This is a serious conversation, and I don’t think this is the right time.”

“Okay.” Rory glances over at him. She runs her thumb over his jaw and smiles when she feels him relax. “We’re gonna be fine, Jess. It’s you and me.”

“We don’t have the best track record,” he murmurs into her hand.

To his surprise, she _ laughs. _ “We’re not eighteen anymore.” He kisses the palm of her hand. “Remember what you said to me, back at Truncheon’s open house all those years ago?”

“I said a lot of things that night.”

“And all of them were true,” Rory says firmly. “But I mean…’it is what it is. You, me.’ You’re still right. But what it is - it’s good now. We’re in the right place for us to work. That’s what it is, and we’re gonna last.”

Jess smiles. “You know I got your back, right?”

“I do.”

He kisses her hand again before she pulls it back. 

(She doesn’t grip the steering wheel quite as tight as she keeps moving, moving, moving.)

**

“Jess! Rory!” Chris cheers when the couple walks through the doorway. “We’re about to get started, so you’re just in time.”

They take their seats where the place cards indicate at a table with Chris, Sara, Matthew, and Sara’s bridesmaids. 

“We get to sit at the special table,” Rory whispers to Jess.

“Perks of being with the best man,” he whispers back with a wink.

Sara hits her spoon against her glass and stands up; the room falls silent. “Now, I don’t know if everyone here knows me-” Laughter ripples through the room- “-but I’m Sara, better known as the Bride, or, to my mother, Beanie. Long story,” she adds, “but that’s for another time. Thank you, all of you, for coming down to see two young and irrelevant kids get married.

“I really am the luckiest woman alive to be married to Chris. I met him seven years ago - a long time ago, right? I met him back when I was working as a secretary at Mount Sinai - you know the one, over on Madison, right? Well, his aunt had just been admitted there after she - and this is a little tasteless, excuse me - fell ice skating and broke her ass, which I’ve been told is called a tailbone, but…” People laugh again.

“She’s funny,” Rory whispers to Jess.

“Anyway, Chris came rushing in and who did he have to talk to, but me, a tired secretary who’s also going through nursing school and getting roughly five hours of sleep a night. He must’ve fallen instantly in love with me-”

“Debatable,” Chris coughs.

“-well, in any case, after we talked, he kept coming back to the hospital-”

“My aunt was a patient.”

“Oh, no one cares about their aunt _ that _ much,” Sara quips, earning some laughs from the guests again. “Even after she was discharged he was coming in, always with a ridiculous excuse. But, after a while, I got the hint and asked him out. And seven years later, here we are.

“Chris, I love you,” she says seriously. “And I can’t _ wait _ to spend the rest of our lives together, through the thick and the thin, through the good and the bad. We will fight the necessary fights, and the unnecessary ones, and still use Jess’ apartment to watch movies in when he’s out of town.” Jess snorts. “I love you. And we will not be having kids!” She adds, announcing it to the room before sitting back down and giving Chris a kiss.

The first course, salads, is served a few minutes later. Chris takes a bite and then says, “So, Rory, for all Jess has told us about you while he was drunk-”

Jess glares at him. “Shut up.”

“-we don’t really know anything about you.”

Rory laughs nervously. “Tonight really isn’t about me…”

“All of tomorrow is about us,” Sara shrugs. “We want to get to know you!”

“What do you do?” Matthew asks, eyebrows raised. 

“Jeez, you sound like my mom,” Chris laughs. “Jess, did you bring home a nice jewish girl?”

Sara snorts. “She wasn’t happy that I was presbytarian. Or, loosely.”

“I- well, it’s complicated,” Rory replies a little awkwardly. “I was a freelance journalist for a while, but after a rut I decided to write a book. Well, actually, Jess gave me the idea for the book this summer. But I’m hoping to get back into journalism as well when we move to New York.”

Chris nods. “I’m assuming you’re a college graduate, then?”

“You do appear very collegiate,” Jess muses. Rory snorts.

“Yeah. I graduated from Yale about ten years ago.”

“Oh, ivy league,” Matthew replies, uncharacteristically impressed. “You might just be one of the only ones at this table that has graduated from college.”

“Hey, I went to Bryn Mawr,” Sara objects.

“All of _ us _ did,” one of the bridesmaids adds. 

“Yeah, well, none of _ us _did,” Matthew replies mockingly, gesturing between himself, Chris, and Jess with his champagne glass. 

“It’s not for everyone,” Rory says with a shrug, glancing over at Jess.

“You can _ say _ that again,” Chris snorts. “I tried it. Went to Boston University for a semester before I dropped out.”

“Better than I did,” Matthew points out. “I didn’t go to college at all. Graduated high school and decided I’d had enough of whatever the fuck _ that _ was.”

“That’s why Jess is our resident degenerate here,” Chris muses, clapping Jess on the back. “But he’s still a paragon for any high school dropout.”

Jess shakes off Chris’ hand. “It’s not that impressive.”

“No, it is,” Rory interjects. “You were a published author at _ twenty-one. _ Built yourself up from nothing.”

Jess mumbles something incoherently and stares down at his salad.

Matthew grins. “I knew we kept you around for a reason, Rory. We’ve been trying to instill that in him for years.”

“Maybe he’ll listen to his girlfriend?”

“That’s doubtful. Have you ever even met him?”

Jess frowns at her and Matthew. “Don’t get me wrong, I’m glad you two are bonding, but maybe pick a different topic.”

“Does he write in all your books?” Matthew asks Rory, ignoring Jess completely.

“Oh my god, yes!” Rory exclaims. “Every single time I lend him one. I had to stop giving him paperbacks because he’d always roll them up and stick them in his pocket.”

“I’ve given up trying to get him to stop.”

“There’s nothing we can do.”

“Don’t even get me started on how he doesn’t have Netflix.”

Rory gapes at him. “Wait, seriously?”

“Hey, it’s expensive, and Hulu has a better TV show selection,” Jess says defensively.

Rory shakes her head. “Jess, _ everyone _ has Netflix.”

“It’s ridiculous. No one needs more than one streaming service.”

“Okay, grandpa.”

“You can get back to praising me now,” Jess says drly, going back to his salad.

Rory laughs and kisses him on the cheek. “We’re just teasing.”

Jess just shakes his head and smiles.

“So, Rory, when are you due?” Chris asks casually.

Sara gasps. “Wait, you’re pregnant?”

Rory flushes; Chris looks at Sara, confused. “I thought I told you that.”

“Nope, you didn’t. But Rory, that’s amazing, really.”

One of the bridesmaids appears dejected. “Oh. Cool.”

Another one of the bridesmaids grins. “You two are having a baby together, then? That’s amazing!”

“Is Jess the dad?” The first bridesmaid asks sullenly.

“Oh- well, uh…he...and the - the baby-” Rory stammers. Jess looks just as uncomfortable as she is. Luckily, Chris swoops in and saves the day.

“It’s not Jess’ - when they got together, she was already pregnant, but they’re raising it together.”

“Oh,” the bridesmaid responds, her tone brighter. Jess grimaces and takes another bite of his salad; Rory almost laughs at the incredibly uncomfortable look on his face as the bridesmaid eyes him.

“You’re Clara, then?” Rory asks. The girl nods, a little taken aback, and glances over at Sara suspiciously. Sara looks the other way innocently.

“You never answered by question,” Chris points out, but he looks quite amused.

“Oh, right. I’m due the first of July.”

Sara smiles excitedly. “That’s not too far off, just a few months.” She shoots Clara, who opens her mouth to say something, a look. “You’re excited, then?”

“Yeah,” Rory breathes with a smile. “It’s a little scary, but…”

“She’s got this,” Jess adds. He squeezes her hand under the table.

She squeezes back. ‘We do, yeah.”

Jess nudges her gratefully with his knee. “We do.”

**

The rest of the dinner goes by fairly well. Clara continues to stare at Jess, who grows continuously uncomfortable as the night goes by. Rory takes it upon herself to run her hand up his thigh to distract him (he shoots her a warning glance which she innocently ignores). Soon enough, however, the dessert plates have been cleared and people begin to leave. 

Jess drapes his suit jacket on Rory’s shoulders as they bid their goodbyes. “See you tomorrow,” he says with a nod to his friends. 

“Thanks for letting me come,” Rory adds sheepishly. “I had a good time.”

Chris smiles. “Yeah, of course. Thank _ you _ for making Jess happy so he’s not sulking around at my wedding.”

Jess scowls.

“Wait, I thought that one was Chris,” Rory says to Jess, gesturing towards Matthew.

Jess raises an eyebrow. “Seriously?”

Rory snorts. “You’re a lot more gullible than I expected.”

It takes Jess a moment before he scoffs incredulously. “I’m wounded. Hurt. Betrayed.”

“Save the dramatics for later,” Rory muses, looping her arm in his and waving to his friends.

They walk like that the rest of the way to the car.

**

“Ten minutes!”

“Where’s the tie? Where’s the fucking tie?”

“Calm down,” Jess scolds Chris. “It’s on that chair.”

“Oh. Right.”

“Chris, dude,” Matthew chortles, “you have _ got _ to get a grip. I haven’t seen you this freaked out since you were asking Sara out for the first time.”

Jess shakes his head. “He was infinitely more freaked out when getting ready to propose.” He continues to fix Matthew’s collar; his friend swats at his hand. 

“I can do that myself.”

“It looked like the work of a kindergartener before I started helping.”

“Shut up.”

Chris stops his pacing; he takes a few steadying breaths before a grin slowly spreads across his face; he has obviously realized something. “Speaking of proposing…” He trails off suggestively.  
Jess raises an eyebrow. “Yes, Mr. Cheshire?”

“_ Proposing…” _

“Spell it out for me.”

“Are you planning on, I don’t know...popping the question anytime soon?”

“I have many questions when it comes to your wellbeing. Like, what the fuck are you doing to your eyebrows? Do I need to call an ambulance for you? ‘Cause I don’t know how fast it’ll get here on short term noti-”

“Shut up for a second, okay?” Chris snaps. “You’re being oblivious on purpose.”

Jess holds up his hands in surrender; Matthew takes the opportunity to dash to the other side of the room so Jess can’t continue messing with his collar.

Jess turns around, facing the mirror so he can fix his own tie and collar. He thinks about four months ago, and the evening of Luke and Lorelai’s wedding, when Rory was fixing his collar for him. He smiles at the memory. (It feels like it was eons ago, millenia - everything that has happened between them since has felt like a lifetime.)

“Any thoughts about proposing to Rory?” 

Jess scoffs. “We _ just _ got back together. If I wanted to scare her off, I’d try something simpler, like wearing denim on denim, or growing a mustache.”

“I’m serious. Do you think you will at any time in the near future?” 

“You’re that eager for another wedding?”

“Jess.”

_ “I look at you and see the passion eyes of May…” _

Matthew groans. “No offense, Jess, but I would rather go deaf than hear you sing.”

“Hey, I need to practice,” Jess objects. “I’m gonna be singing lullabies soon enough, and I have to practice if I don’t want to rupture the baby’s eardrums or something.”

Chris just shakes his head, a glint in his eyes. “So?”

Jess hesitates. “Not in the immediate future. But, someday...I don’t know. We’re happy as we are right now, and we’re going to be happy living together with a kid, so...I’ll see where it goes.”

“You _ are!” _Matthew exclaims gleefully.

“Did you not listen to what I just said?”

“I did, but I also know how Jess-speak works. He’s definitely thinking about it.”

With a grin, Chris claps him on the shoulder. “Can’t wait to see what grand proposal the author comes up with.”

“You know I’m not one for grand, over-the-top gestures. Or are you getting me confused with your other friend Jess?”

Chris raises an eyebrow. “Tracking down a girl to show her your book after not seeing her for a year and a half?”

“Chasing her through the streets just to tell her you love her?” Matthew chips in.

“Asking her to run away with her?”

“Moving back to a town just for her?”

Jess glares at them through the mirror. “Okay, okay. Let’s not forget who today is _ really _ about.”

“Who?” Chris asks innocently.

“You’re getting _ married _ today.” Jess chuckles. “I’m happy for you, man, I really am.”

Matthew smiles. “It’s been a long time coming.”

Chris looks at his two friends for a moment before breaking out into a wide grin. “I’m getting married, huh?”

“In seven minutes,” Jess confirms.

“I’m getting married,” Chris repeats in wonder. “_ Married.” _

**

Sara is radiant as she walks down the aisle, flanked by her parents, her eyes unmoveable from Chris’. It’s hard to tear her eyes away, but when Rory catches Jess’ gaze from the altar, her stomach bottoms out. His warm brown eyes are a little wet and full of something so familiar. 

_ I love you, _ he mouths.

She grins and wipes her eyes. _ I love you. _

Vows are exchanged, rings are given, and Chris stomps on the glass to the welcoming cheers of the guests. And, just like that, it’s over. 

**

Rory’s phone begins to ring the second they arrive at the reception hall. She tells Jess to meet her inside - speeches won’t start until everyone has arrived and settled - and he kisses her on the cheek and promises to save her a seat. 

She glances down to see who’s calling and her stomach drops.

“What is it?” She asks warily, glancing over at Jess. He’s talking to Matthew and laughing; she almost smiles until she remembers who is calling.

“Woah, Ace, thought you’d be more happy to hear from me.”

Rory sighs. “You’re right. Sorry, I’m at a wedding, and the reception is starting soon, and Jess is saving me a spot, so…”

Logan pauses. “Jess, huh?”

_ Guess this is all coming out sooner than planned, _ Rory thinks to herself. She takes a deep breath and puts on a brave face. “Yeah, Jess.”

“You’re going to weddings with Jess.”

“Well, just the one. We’ve been blacklisted from all the others.”

Logan doesn’t laugh. “What’s going on, Ace?”

“I…” Rory closes her eyes and purses her lips. (Don’t back down now.) “Jess and I are...together. We’re dating.”

“Way to bury the lead,” Logan laughs humorlessly. “When were you planning on telling me? Your own wedding?”

Rory sighs. “I was going to, I swear, okay? This _ just _ happened, like, not even a month ago.”

“We’re having a kid. I have the right to know who’s going to be in their life.”

“Yes, but-”

“What else haven’t you told me? Is it twins? Are you moving to Timbuktu? Anything else concerning Jack?”

“It’s _ Jess,” _Rory snaps. “But you’re right. I should’ve let you know, I know, I just...I’ve been happy, Logan, and I’ve been trying to savor the time I have with him, and...and these are all excuses. I should’ve told you. I’m sorry.”

“It’s okay.”

Rory bites her lip. Something about this doesn’t feel right, has never felt right - “No, it’s not.”

“You apologized, Ace, I don’t see what-”

“No, that’s not it,” she says a bit more forcefully. “Why the hell do _ I _have to apologize? Has it - has it always been like this between us? Will it always be?”

“What do you mean?”

“When will I let _ my _ needs matter just as much as yours? When will you stop acting like they don’t? You’d have known sooner or later that I’m with him, Logan, but on my _ own _ terms, not yours.”   
“Rory-”

“You wanted out, which is fine, like I said, but you don’t get to - to - maybe I should be thanking you instead, because I’m a lot happier now than I was sneaking around with you! You were engaged then and you’re engaged now. Don’t act like you’re on some moral high ground here.”

There’s silence on the other end for a moment before Logan speaks. “I was just calling to get an update on the pregnancy,” he says evenly. 

Rory presses her hand to her temple and sighs. “Right. Everything’s good, we’re both healthy, due date is July first. Anything else?”

“I guess not. Just…” Logan sighs. “Why him, Ace? Why _ him?” _

Rory hesitates. “I don’t like being the one that makes people leave the room,” she says softly, after a long pause.

“What?”

“I don’t like being the one that makes people leave the room,” she says, a bit more forcefully. “I don’t want to be the one who cheats or fails or makes promises that I can’t keep. I don’t want to do and say things that make people walk out, whether they’re disgusted or ashamed or angry. This...this affair we were having? I became the other woman, again, which was my choice, again, but it was yours too, again. I became this woman who makes people walk out. But Jess…Jess doesn’t make me be that person.”

“And what’s his role going to be, huh?” Logan demands. “Who’s he going to be to _ our _ child?”

“He’s going to be the dad.”

“This isn’t dress-up, Rory,” Logan retorts angrily. “You can’t just give him a tie and a briefcase and play house.”

“There’s a _ plan, _ Logan.”

“Oh, well, enlighten me, then.”

“We’re moving to New York. His publishing house is moving there, too, so he’ll be working. I’m just waiting to hear back to places I’ve applied to. And he’s going to be a _ good _ dad, Logan,” she adds.

“He’s _ not _the dad. I am.”

“No,” Rory snaps. “You may be the father, and this kid may have your DNA, but you are not the dad. You’re not going to be the one who changes their diapers or reads to them or sings lullabies in a god awful singing voice. You won’t be packing their lunches or braiding their hair or anything else a dad does because you didn’t want to be there. Jess doesn’t have to be there, he has no obligation to raise a kid, but he _ chose _ to, and he _ wants _ to, and he’s not going to leave.”

“He’s left before.”

“That was years ago.”

“Rory-”

“No,” she says firmly. “Don’t. You’ve said enough.”

Logan clears his throat. “Fine. Have fun at the wedding.”

“Fine.”

Rory hangs up and angrily shoves her phone in her purse. She goes into the hall and finds Jess sitting at a table; he motions for her to sit down. 

“Who was it?” He asks, leaning in and murmuring when she sits down.

“No one.” He raises an eyebrow. “I’ll tell you later.”

]Chris gestures towards him; Jess nods and hits his spoon against his glass to get everyone’s attention. Rory looks towards him and listens attentively.

“Hey, everyone, I’m Jess. I’m the guy who’s apartment they sublet for free to use my Hulu account to watch movies because I won’t give them my password.” Everyone laughs. “I’ve known Sara almost as long as Chris has - although I’ve been hearing about her since they met - but I’ve known Chris even longer. This is about to get fairly self-centered, so feel free to tune it out.

“As many of you may know, or not know, I am an author. Yeah, published my first book at the age of twenty-one. But none of that would have been possible without this guy. I met Chris back in 2005; I was living in New York at the time, and Chris was in town with his business partner, Matthew. They had recently opened up Truncheon, and I met them one night at the bar I worked at, and we got to talking. They eventually published this book I’d been writing, and long story short, I started working with them and we’re still going strong twelve years later. 

“Without them, I wouldn’t be anyone. Probably be lying dead in a ditch or something else tragic, but something none of the Beatniks had tried. I was...troubled, alone, broken...but Chris helped me put myself together again. And to see him getting married, see him _ this _ happy with the woman he loves…” 

Jess clears his throat. “I think Kerouac said it best: ‘Love is all.’ I add: love saves, it comforts, it _ encompasses _you. You two have written a beautiful love story, and this is only the beginning.” He lifts his glass. “To Chris and Sara.”

“To Chris and Sara,” the room echoes.

Jess takes a seat and dabs at his eyes. Rory looks at him in wonder. “That was beautiful, Jess. Really.”

He cracks a grin. “Easier to write good things about love when it’s doing right by you, I guess.”

She kisses him on the cheek and doesn’t let go of his hand through the rest of the speeches.

**

Soon enough, the dance floor opens up, and the sound of _ Songbird _ fills the room and leads into the first dance. 

“They Fleetwood Mac fans?” Rory asks, somewhat absentmindedly as she watches Chris lead Sara onto the dance floor.

Jess shrugs. “As much as the rest of us.” He glances over at her. “You okay?”

Rory frowns. “Why wouldn’t I be?”

“You got a little…” Jess brushes under her eye and Rory realizes she’s crying.

“I’m okay. Guess I’m an easy cry when it comes to weddings. And there’s just something about this song…”

Jess nods for her to continue.

“It’s just...beautiful. He loves this woman more than...more than anything, and it’s this genuine love, real, raw, vulnerable. ‘To you, I’ll give the world.’ It’s authentic and so honest.” She shakes her head. “There’s something so sad about it at the same time, though. ‘And I wish you all the love in the world, but most of all, I wish it from myself.’ Longing and loving and in the end, he just wants her to know he loves her. ‘And I love you, I love you, I love you like never before…’” She trails off.

Jess doesn’t reply, his eyes fixed on her. She swears she sees a million emotions flash through them in one moment. 

He grabs her hand and squeezes it. “Yeah.” A short, loaded answer. 

_ Songbird _ fades out and leads into the opening of _ Kiss Me. _ Other couples stand up and go out to the dance floor. Rory looks over at him.

“Let’s dance,” she declares, standing up and offering him her hand.

Jess’ lips quirk up into a smile. “As you wish.” 

It feels almost like it did at Luke and Lorelai’s wedding, but there’s something so much more intimate about it when she wraps her arms around his neck and he wraps his around her waist, his hands on her lower waist. They begin to move. 

“Logan called me,” she says suddenly, surprising Jess. “About the pregnancy and everything. I mentioned you and he was angry, angry that I didn’t tell him about us...I told him off. But it did get me thinking about us and the conversation we had on the way to the dinner last night.”

“What is it?” He murmurs, mouth too close to hers. 

She takes a shaky breath. “How are you feeling about all this?”

He presses his forehead to hers, jaw tight. “He’s the father, Rory. I’m not, not in the same way. Not in...not in the way that _ counts.” _He swallows. “I guess I just feel...like an imposter. A stand-in.”

“You don’t need to be insecure,” Rory says softly. “Jess, you’re _ here. _ You’re _ willing. _ That’s all that matters.”

Jess nods; she can tell he’s still having some trouble accepting it.

“I understand, though. I do,” she adds quickly.

He gives her a grateful look - still pained, still struggling, but grateful. Rory saves him from saying anything more by leaning in and kissing him. 

_ Lead me out on the moonlit floor / lift your open hand / strike up the band and make the fireflies dance / silver moon’s sparkling... _

  
  


**Notes for the Chapter:**

> jess and rory needed to go to more weddings i think


	26. All Or Nothing At All

**Summary for the Chapter:**

> Jess and Rory go to a doctor's appointment. Truncheon moves locations.

**Notes for the Chapter:**

> Four more chapters after this...

Rory drives back to Stars Hollow the next morning, kissing Jess goodbye and kissing Matthew on the cheek quickly before he can stop her. As Jess watches her drive off, he feels that familiar pit in his stomach, but he shakes it off and goes back into his apartment.

“Thanks for breakfast, by the way,” Matthew says as the door clicks shut behind them. “Sorry for, you know, interrupting your last morning with her before she had to leave.”

Jess shrugs. “No biggie.” He falls back on the couch and closes his eyes. “God, I can’t believe Chris is going to be in _ Curaçao _ for the next two weeks.”

“I would literally give anything to be in the Caribbean for two weeks. The longest I’ve been there is when my plane had to emergency land for two hours.”

Jess snorts. “Must’ve been quite the vacation.”

“Yeah, well…” Matthew shakes his head and goes quiet. “So, everything’s good with Rory, then?”

“Yeah. Why?”

“I don’t know. I just…” Pause. “I know you, Jess. I can tell when something’s a little off.”

“Are your spidey-senses tingling? Cause-”

“Hey, Jess?” Jess raises an eyebrow. “Shut up for a second, okay?” Matthew sighs. “Look, dude, I’m just worried about you. You’ve always been a little...insecure when it comes to her, and with this baby...I just want to make sure you’re good.”  
Jess groans. “Why does everyone suddenly want to talk to me about this? I swear…”

“Because there’s something on your mind that you’re hesitant to talk about,” Matthew insists, “and it’s _ not _ going to go away until you do.”

Jess doesn’t say anything.

“Jess.”

“Fine.” Jess sits up a little. “I’m excited to raise this kid with her, I am, I just…” He swallows. “I can’t help but be reminded every time that it’s not really _ my _ kid. God knows who will use that against me. Logan, her mom…”

“Why does it matter?” Matthew asks. “You’re going to be the one that’s in the kid’s life. Isn’t that all that matters?”

Jess fidgets uncomfortably. “Doesn’t feel like it,” he mutters.

“This could just be all in your head.”

“Or it could not be.”

Matthew grimaces. “It’ll only be real if you let it be.”

“Yeah, well…”

“You love her, don’t you?”

“I do.”

“Then…” Matthew sighs. “You know her, Jess, more than a lot of people do, I’d think. She chose you, right? Then obsessing over all this is pointless.”

Jess stares down at his shoes. “But-”

“Why is this so hard for you, Jess?” Matthew asks gently. “Why can’t you accept that things might actually be going well for you this time around?”

Jess takes a deep breath. “I’ve never had a great track record with her, especially not when I’m compared to her exes. By Rory, and everyone around her...I was lesser than. Second tier. What if that’s what they’re all thinking? ‘Why is _ Jess _ raising this kid with her? Shouldn’t it be Logan?’ I’ve never done anything but hurt her, and now...how could any of them trust me? And am I really a better choice at all?”

“You don’t think you’re the right choice for her?” Matthew clarifies after a pause.

“I’ve never been before,” Jess mutters.

Matthew bites his lip. After a moment, he stands up and sits next to Jess. “I’m sorry, man. I didn’t realize it all...it all went this deep.”

Jess stares up at the ceiling and blinks. “Yeah, well…”

“Come here.”

“We are _ not _ hugging.”

“Shut up, okay?”

“Matthew-”

“Shut up.”

  
  


**

It’s three days later when she finally sees Jess again. It’s a long drive up to New York to her new hospital, and she’s feeling a little cramped by the time she parks in the lot. She’ll miss the Jeep up in New York, of course, but she has to admit, it’ll be nice not having to drive everywhere when she’s living in the city.

It’s a new hospital, so she struggles a bit finding her way to the correct office. She finally finds it, and of course, he’s already waiting for her in the waiting room. “Finally found your way up?” He asks amusedly in lieu of a greeting.

She sticks her tongue out at him. “Shut up. It’s a maze here, okay?”

He simply shrugs. 

“Let me check in, and then you can continue giving me a hard time, okay?”

“Be my guest.”

“When did you get here?” She asks after checking in, sitting down in a chair next to him.

He shrugs. “Ten minutes ago, maybe? Not too long ago, but long enough that I’ve been cornered by at _ least _ three sick children.”

“Aw, that’s cute. You must come off as _ very _ parental.”

Jess looks slightly nauseated. “Mhm.”

Rory laughs. “You’ll be fine.”

“One had the chickenpox, I think.”

“Jess, you’ve had it before.”

“Could’ve been measles.”

“You’re a child.”

“Mumps.”

“Are you suddenly a hypochondriac or something?”

“Hey, if you want any more kids, you should be concerned. Mumps can sterilize men.”

Rory rolls her eyes. “Let me know when you’re done being dramatic.”

Jess cracks a smile and gives her a quick kiss.

Rory raises an eyebrow amusedly. “I thought you had the mumps.”

“You love me, you’ll risk getting them.”

She smiles. “Thanks for coming.”

Jess wraps an arm around her shoulders and pulls her closer; she rests her head on his shoulder. He plants a kiss on the top of her head. “Wouldn’t have missed it.”

Jess was right about one thing: there are a _ lot _ of kids in the waiting room. A few run around, playing with the assorted toys strewn around. Some women have babies in their arms or in carriers, others still pregnant. One gives Rory a reassuring smile; she must look more nervous than she thought. 

“Rory Gilmore.” 

Rory turns her head at her name being called. A nurse stands by, looking a little impatient; Rory gets up and goes over, Jess not too far behind.

They follow the nurse down a hallway until she stops in front of a door. “The doctor will be with you in a few minutes,” she informs them before turning and walking back towards the waiting room. 

Rory changes into the paper gown as quickly as she can, face on fire; Jess laughs a little under his breath. She sits down as he looks around the room a bit. “I wonder what this does,” he mutters, picking up an absurd-looking medical tool and twirling it around in his hand to examine it.

The door opens, startling Jess - he drops the instrument immediately and steps away. A woman walks in and shuts the door behind her. “You’re Rory Gilmore?”

Rory nods. “Yeah.”

The doctor smiles gently. She seems nice, but it’s a shame Rory had to leave Dr. Kim - she’d kind of reminded her of Lane. “I’m Doctor Karim,” she says. “It’s very nice to meet you, Rory.”

Rory smiles nervously and doesn’t say anything. 

Doctor Karim checks Rory’s chart. “So, five months into the pregnancy. Mom and Dad, you excited?”

“I’m not-” Jess starts, but Rory cuts him off.

“Yeah, we are,” she says brightly, squeezing Jess’ hand. 

Jess swallows and smiles weakly. “We are.”  
“Alright, well, I assume you two know the drill. Ready to see your baby?”

Rory’s almost used to the ultrasound gel by now, almost, but she still has to bite her lip from giggling a bit when it’s applied. Jess taps his foot anxiously as they wait, wait, wait, and then - and then it’s quiet.

Rory’s familiar with the little leap in her heart when she sees the baby on the screen, it’s the same every time - she thinks she falls a little more in love with the unborn baby every time. 

She sneaks a peak at Jess. “Huh,” he murmurs, a dazed expression on his face. He squeezes her hand somewhat absentmindedly, but Rory smiles to herself all the same. 

**

She still doesn’t want to know the sex, and neither does Jess - although she makes sure to remind him as she’s getting redressed that it wouldn’t have mattered either way, it is _ going _ to be a surprise, to which he just laughs. 

She kisses him goodbye in the parking lot before getting into her car. “Only three days, Jess.”

He smiles, hands in his pockets. “Three days.”

She drives off and all of Jess’ uncertainty he’d been struggling to hold back starts to settle in the pit of his stomach. He’d managed to keep it at bay during the appointment, but he can’t shake it now. That’s not _ his _ kid, the one on that screen, the picture in his pocket right now. Does he have the right to love it? Does he have the right to treat it as his own?

He pushes these thoughts away and puts his car into drive.

**

All the boxes have been packed, labeled, taped, unpacked, repacked, relabeled and retaped. The building feels empty as the last few are carried out and to the truck Matthew reluctantly rented. There’s an unwelcome feeling in Jess’ throat as he watches, no matter how many times he tries to swallow it down. 

“That’s the last of it?” Matthew asks, out of breath and sweaty.

Jess nods, drawing circles on the flooring with his foot. “Yep. That should be it.”

The door opens, and Chris, Sara, and Rory walk through, breathless as well. 

“Jess, how do you have _ that _ many books here? I thought the entirety of the Schwarzman branch was in your apartment.”

The corner of Jess’ mouth quirks up in amusement. “I had to mark my territory somehow.”

Matthew shakes his head. “Too heavy. Settle for peeing like the rest of us.”

“Okay, gross,” Rory replies, nose scrunched up. She walks over to Jess and slips an arm around him, leaning in. 

He kisses the top of her head. “We should get moving. It’s a long drive.”  
“It’s only an hour and a half,” Matthew counters.

“Okay, just because you’re from the middle of nowhere doesn’t mean it’s not a long one from the rest of us,” Chris retorts. 

“Chicago is _ not _ the middle of nowhere.”

“It’s surrounded by corn.”

“That’s objectively not true.”

“Both of you, shut it,” Jess reprimands. “How I’m gonna survive an hour and a half drive with these lunatics, I don’t know,” he says in a lower voice to Rory.

She smiles and shakes her head. “I think you’ll manage. Just turn up the music really loud if they get too rowdy.”  
“Noted.” 

“You didn’t forget anything?” Sara asks. “Every box is accounted for?”

Jess nods. “You’re lucky your husband is a compulsive list-maker. Almost at Rory’s level.”

“Hey!” Chris and Rory object in unison. 

“We should get going,” Jess says, ignoring them.

Matthew lets out a deep sigh. “I’m gonna miss this place.”

Chris nods solemnly. “Remember when Matthew threw up over there?”

“Alright, we’re going!” Matthew exclaims pointedly. “We need to be at the building by four.”

“I’ll catch up with you guys, okay?” Jess says as his friends start moving. “I just wanna…” He trails off.

Rory smiles and kisses his cheek. “Meet you in the car.”

The door closes shut, and Jess is alone. His eyes sweep over the room, trying to memorize every detail. Jess isn’t the sentimental type, he never has been, and he _ never _ imagined that one day it would be this hard to leave a place. As a kid, he was always running, always revved to go, go, go, and never look back. He’d never have thought in a million years that it would ever be this hard.

He walks around the room, slowly, hand brushing the railing of the stairwell as he walks past it. This building, this room, this _ place _\- this is where he turned his life around, pulled himself out of the gutter and built himself up from square one. 

This is the place that took him in when he thought there was nowhere left for him to run. He wrote himself a future, a _ life, _wrote himself into a world with friends that became family. 

He looks out at the room. 

It’s empty now, everything gone - just a room.

He clears his throat, gives it one last look, and walks out the door for the last time. 

  
  



	27. The Lorelais Can Wait

**Summary for the Chapter:**

> Four months later, Rory goes into labor.

**Notes for the Chapter:**

> This ones kinda short but...yep

** _About four months later_ **

** _June 30th, 2017_ **

Jess uselessly tries to force the screw in, to no effect; it clatters to the floor the second he lets go. He picks it up again, turning it over in his fingers before trying again. When it falls again, he lets out a frustrated groan.

“Having some issues there?”

Jess looks up; Rory watches him amusedly, leaning up against the doorframe. 

“Ha ha,” Jess replies dryly. “Such a comedian.”

“This is nothing new about me.”

Jess shakes his head with a smile. He attempts with the nail one more time and watches it hit the floor yet again. “That’s it. This thing is just gonna have to assemble itself. I’m done.”

“It can’t possibly be  _ that _ hard, can it?”

He gives her a look.

“Okay, okay.” Rory smiles with a little laugh. 

“I’ve been trying to screw this in for  _ way _ too long.”

Rory smiles. “Thank you,” she says sincerely.

Jess cracks a grin. “No biggie.” 

She moves a little further into the room, watching him continue to work. “The nursery doesn’t look half bad, though.”

He looks up at the sea-green walls and mobile hanging above where the crib is going to be. “I think we did a good job, all things considered.”

“Well,  _ you _ did a good job. I’ve been sitting around watching TV and reading every day since my maternity leave from CBS started.”

Jess smiles. “Bet they were sad to see you go.”

“The cake  _ was _ pretty good.”

“No doubt about it. Carol outdid herself with that frosting.”

Rory gasps. “I  _ knew  _ you were the one who finished it!”

“Guilty as charged.”

“And trying to pin it on Chris!” She exclaims, shaking her head. “For shame, Mariano. For shame.”

He grins. “My sincerest apologies.”

“Yeah, well…”

“Bet you’re ready to get that out of you,” he says, gesturing to her stomach. “Day before your due date and all.”

She shrugs. “It’s actually not that bad. I might actually kinda miss it.”

“Are you kidding me? You almost bit my head off for daring to throw away our Thai leftovers the other day.”

She shoots him a look. “In my defense, I would’ve done that even if I wasn’t pregnant.”

“What about when I deleted your recording of  _ The Good Place _ from the DVR?”

“Alright, what I’m getting from this is that you’re a nuisance to live with.”

“Well, you wouldn’t kick me out, would you?”

She looks at him lovingly. “No I wouldn’t.” She leans up against the wall, crossing her arms across her chest. “So, what’s the agenda for the rest of the day?” 

“After I put the finishing touches on the nursery, movie night?” He suggests.

“Sure. What were you thinking?”

_ “Rear Window.”  _

Rory groans. “Not  _ again.” _

“Hey, I agreed to watch  _ Freaky Friday _ last night. You owe me.”

“I still don’t get why you hate that movie.”

“Out of principle, of course.”

Rory shakes her head. “You’re impossible.”

“So?”

She rolls her eyes at the expectant look on his face. “Fine. But,” she adds sternly before he can gloat, “we’re ordering Indian food.”

Jess groans. “We’ve had that twice this week  _ alone.” _

She grins. “I’m afraid it’s non-negotiable.”

“Have I mentioned that I hate your cravings?”

“Is it a deal?” 

“Deal,” Jess relents, giving her another look. “But you order it.”

“Okay,” Rory says, straightening up with a slight grunt. “My phone’s in the bedroom. And while I’m there, I’m getting you a razor.”

“You really hate the beard look that much?”

Rory scowls. “It tickles.”

“If you’re making me eat Indian  _ again,  _ the beard stays.”

Rory laughs quietly as she leaves the room. Jess gets back to working on the crib, finally starting to get the screw in when he hears Rory call out, “Jess?”

He swears under his breath, dropping the screw yet again. “Yeah?”

Pause. “I think my water just broke.”

“Shit,” Jess curses, scrambling up off the ground and towards their bedroom. Rory stands frozen by the dresser, a panicked look on her face. “Guess we have to cancel movie night,” she jokes, but she’s still a little shaken.

“Okay, I’ll grab the bag, call a cab - you just sit down, okay?” He tries to give her a reassuring smile, not all that sure it’s convincing; he’s already pulling his shoes on. “It’s gonna be okay.”

She takes a deep breath. “Okay.” 

Running to grab their things, Jess dials the number for a cab, only now realizing how fast his heart is beating. He told Rory it was going to be okay, and he believes it, he does - but he’s scared. So scared. 

Oh, god, he’s  _ terrified. _

**

The cab comes soon enough, but the traffic is moving  _ so _ slow or maybe that’s just the fact that Jess swears time could not be moving any slower than it is, right now, currently. Rory’s only a little frantic, but he knows he’s about two seconds away from going off the rails.

“Can you call my mom and Luke?” She asks, face contorted into a grimace; just for the record, she is  _ not _ a fan of these contractions. 

Jess nods and pulls out his phone without another thought. He decides to call Lorelai’s number, and taps his foot anxiously as he waits for her to pick up.

“I’m sorry, but the number you’re trying to reach is no longer available. Or something.”

Jess rolls his eyes with a little scoff. “You’re very funny. Nearly Redd Foxx funny.”

“Ah, yes, but I’m just as dirty.”

“I don’t doubt it.”

“So, what warrants the call, Mariano?” Lorelai asks. “Everything all good on the home front?”

“Yeah, it’s just, uh,” Jess stammers, glancing over at Rory, “Rory just went into labor. We’re on our way to the hospital - her contractions about 15 minutes apart.”

There’s silence on the other end. 

“Labor. You know what that is. You’ve been in labor before, right?”

“Alright, don’t get smart with me, Mariano.” Pause. “What hospital are you going to?”

“New York Presbytarian.”

“Okay. Luke, get your ass out here, Rory’s in labor!”

Jess glances warily out the cab window. “There’s a lot of traffic.”

Lorelai laughs. “Don’t worry. She’s not going to give birth in the cab.”

“God, don’t put that thought in my head.”

“I don’t have to tell  _ you _ to breathe, do I?” Lorelai asks amusedly. “You sound a little freaked.”

“I am  _ not  _ freaked.”

“Just a little bit.”

“I’m not-“

“If you were, I’d understand.” 

“I-“

“Jess?” 

He sighs. “Yes?”

“Keep an eye on our Rory until we get there, okay?”

He smiles. “You can count on me.” It feels weird, saying that, still does, and probably always will. He spent so long being unreliable, especially when it came to Rory, that now, it still feels a little foreign to say. But that doesn’t make it any less true.

“I assume she doesn’t want to talk.”

Jess glances over at Rory, who shakes her head, still grimacing. “You’d assume correctly.”

“Well, we’ll be over there as soon as we can. Getting in the car as we speak.”

Jess nods. “Okay. Drive safe.”

“Drive safe? Words I never thought I’d hear from _ Jess Mariano.” _

He smirks. “Thanks,  _ grandma.” _

“Shut up, you.”

**

“Where are they?”

Jess smooths down Rory’s hair gently, kissing her temple. “There’s a lot of traffic on I-95.”

Rory scrunches up her face, gripping his hand tighter. “It’s been almost three hours.”

“It’s gonna be-“

“If you say ‘okay’ I’m going to deck you in the face,” she warns.

Jess holds back a laugh. “Alright.”

“God, I  _ hate _ this,” she moans, leaning back with a grimace. “I’d like to have a word with Eve about all this. Was the apple really worth it?”

“You’re not even at the worst part yet.”

Rory glares at him.

“Not helping?”

“You’re not, no.”

Jess sighs takes a seat in the chair beside the bed. “She’s calling every thirty minutes with an update.”

“She’s supposed to go in the delivery room with me.”

“I know. She’ll be here soon enough, I promise.”

Rory winces and bites her lip. “You’ve got these contractions down,” Jess says; she manages a weak smile.

“Jess?” She says, voice quiet.

“Mhm?”

“Will you...will you go into the delivery room? With me? Until my mom gets here?”

He smiles gently. “What, you’d think I let you be in there alone?”

She returns the smile. “No, I didn’t.”

“Of course I will. But don’t squeeze my hand so hard that you break it.”

“I’ll try.”

**

She’s squeezed Jess’ hand so hard, it’s probably black and blue by now, but it’s fine, it’s okay, really, it is; he’s told her she’s doing so well - and she is, really, doing  _ so _ well - too many times to count as the hours or minutes or whatever it is goes by. He doesn’t leave her side.

When the door swings open and Lorelai comes in, a frazzled nurse running after her reminding her she can’t be in here, not yet. She meets Jess’ eyes, and there’s a look in them that he’s never seen directed at him before, not from her - but then she looks over at Rory and the moment is broken.

Jess kisses Rory on the temple and leaves the room, letting her hold her mother’s hand instead, which is the way it should be, anyway. It’s interesting, he thinks, collapsing into a chair beside Luke, how history tends to echo the way it does, never exactly the same, but the similarities evident.

That’s always the most important part, anyway. 

**Notes for the Chapter:**

> And the countdown continues...3 chapters left...


	28. The Waiting Room

**Summary for the Chapter:**

> Revelations are had in the waiting room while Rory is in labor.

**Notes for the Chapter:**

> Place your last bets now - girl or boy? You'll find out at the end of the chapter...

Jess falls back into a chair next to Luke with a grunt, suddenly feeling very exhausted. His uncle glances over at him somewhat anxiously. “It’s all going okay, then?”

Jess grunts in agreement. “It’s good. She’s doing great.”

“Good,” Luke says with a nod. “Good.” 

“Would you cut that out?” Jess asks, gesturing towards Luke’s leg that he’s been bouncing for the past minute. “I hate the noise of denim against denim.”

“What, did your makeout days with Shane in the back of your car traumatize you _ that _ much?”

Jess doesn’t open his eyes. “Hilarious.”

“You _ know _ how I feel about hospitals.”

“Relax. I can get Sandra Oh over here if it’ll make you feel any better.”

“What?”

“Nevermind.”

Luke scoffs and shakes his head. “One of these days, you’re going to have to stop making these references, for my own health.”

“Mental or physical?”

“My mental and your physical.”

“Noted.”

Pause.

“You’ve got a little something…” Luke reaches over to thumb at Jess’ beard; his nephew swats his hand away with a scowl.   
“Stop that.”

Luke chuckles. “You look _ cool.” _

“Hey, I get enough grief from Rory about it already, so cut it out,” Jess warns him.

“Does GQ know about you?”

“I’m ignoring you now.”

Luke chuckles to himself, apparently satisfied. Jess rolls his eyes.

A couple walks by, a man and a woman, the man holding a baby and the woman looking very tired but very happy at his side. It’s a nice image, sure, and Luke, pleased that none of them look ill or contagious, glances over at Jess. His brow is furrowed in a way that is all too familiar.

“Jess?”

“Mhm?”

Luke fidgets uncomfortably, thinking out his approach. “You know, there was this one time I saw you when you were about five,” he begins after a pause. “It was after - I think it was Danny - David? Left. Daniel - Don-”

“Dom,” Jess finishes for him.

“Right.” Luke shakes his head. “Well, anyway, it was after Dom left, and your mother was freaking out, of course, so I drove up to the city to do some damage control.”

“Are you expecting me to remember any of this so we can look back on the good old days?” Jess asks dryly. “Because if that’s what you’re going for, I don’t think anything from age one to twenty is going to get you anywhere.”

Luke softens a bit at Jess’ tone. “Just...listen, okay?”

Jess raises his eyebrows. “Yes?”

“I came to your guys’ apartment, and your mother was a mess. She’d been drinking and you hadn’t had a proper meal to eat for a week. When I got there, your mother was crying, and...you were trying to comfort her, I guess.”

“Ah, yes, that was before I learned that this is just how Liz was,” Jess interjects, looking uncomfortable. “That it was best to just let her do her thing and fend for myself.”

Luke looks at him with something far too close to pity. “You didn’t understand what was going on, then, Jess. You were a _ kid _ whose mother had been hurt, again, and you’d lost yet another father figure-”

Jess scoffs. “I don’t think Dom was anything _ close _ to a father figure.”

“And _ anyway,” _ Luke says pointedly, “I remember that even though she’d been left by the scumbag and rendered pretty much useless, you were taking it upon yourself to feed yourself, her, clean the apartment...you were _ five. _ And you still tried to fix it.”

Jess’ jaw clenches, but he doesn’t say a word.

“My point is...you’re a fixer, Jess. Maybe you forgot that for a while, let the world keep you down and push you to your lowest, but not now. You’re...you’re dependable. You do what’s best for everyone around you. And,” he adds in a quieter voice, “I know for a _ fact _that you’ll be the dad you never had.”

Jess sits there for a moment, silent, and Luke begins to worry that he pushed too far, but then Jess clears his throat, wipes at his eyes, and manages a weak smile. “Thank you, Luke.”

Luke nods.

After a moment of silence, Luke asks, “Was Dom the one that ended up in prison?”

Jess laughs. “I’m pretty sure Dom was in the mafia.”

“It was never proven.”

“He’d come home smelling like cigars and blood.”

“So what? He could’ve been a butcher or something.”

“He helped run a casino in Las Vegas.”

“Alright.”

“He had a pizza store that was _ definitely _ a front.”

“You’re hilarious.”

“I’m not kidding.”

Luke raises his eyebrows. “You’re serious?”

“I distinctly remember him calling up an ‘associate’ with the ‘weather report’ multiple times.”

“Who was he, Sally Tomato?”

Jess eyes him amusedly. “Wow, look at you, referencing classic movies casually.”

Luke grunts. “Lorelai made us watch _ Breakfast at Tiffany’s _ last night.”

“That makes a _ lot _ more sense. You’re more or less uncultured.”

Luke elbows him in the side.

**

Time moves very slowly in waiting rooms, Jess notes, watching the clock on the wall move second by second. He tried to read, he really did, but he just couldn’t focus.

He can’t help but dwell on what Luke said; how did his uncle know just like that what Jess needed to hear? He can’t erase the insecurities, no matter how much he tries, but part of him is eased by Luke’s words.

Maybe he _ is _ making it a mission to be the father he never had. Maybe that’s the one thing he can do, break the chain of lousy parentage and do something _ good. _ Do something _ right. _ It’s only still a little strange to feel that way now, but he thinks maybe he’ll get used to it. 

“Don’t make me talk to your supervisor,” an all too familiar voice shrills, snapping Jess out of his thoughts. “I’m here to see my granddaughter, Rory Gilmore. Could you look her up any slower? I’m sure I have all the time in the world to kid around and wait for you to point me in the right direction.”

Jess and Luke make eye contact - _ your turn, _ Luke mouths, and Jess shoots him a glare. He stands up reluctantly and makes his way over to Emily, somewhat apprehensively.

“Emily?”

She whips her head around. “Oh, Jess, it’s you. Could you tell this woman I need to see my granddaughter and great-grandchild immediately? Apparently, she thinks this is all some sort of joke.”

“Rory’s still in labor,” Jess informs her calmly. “Actually, you’re the first person to get here, besides Luke and Lorelai.”

“Oh? And where is Lorelai?” Emily asks, scanning the waiting room, momentarily forgetting about her grievances with the receptionist.

“She’s in there with Rory.”

“Oh.” Emily holds her chin up a little higher. “Alright, then, I suppose it isn’t _ that _ big of a deal.”

Jess shoots the receptionist an apologetic look before leading Emily over to where Luke is sitting, on the verge of dozing off. Emily looks a little out of place as she removes her coat, looking around.

“The traffic on the way here was abysmal,” she announces. “I mean, it was backed up for _ hours _ and _ hours - _ and just because some lunatic decided to have a _ stroke _ in the middle of the highway.”

Jess chokes on his sip of water. Emily pays no mind to his coughing. “Anyway, I suppose it isn’t the end of the world, considering the baby hasn’t even been born yet. How long has it been?”

“About three hours?” Jess offers, still coughing. 

“That isn’t too bad, then. My labor with Lorelai took _ hours _ and _ hours, _although I guess that…” She continues talking, but Jess zones it out, closing his eyes and leaning back in his chair. 

“Jess.”

He cracks one eye open. “Yes, Emily?”

“You know, it’s very rude to doze off while someone is talking to you.”

“My sincerest apologies to Miss Manners.”

Emily rolls her eyes. “Are all of the men in your family this sarcastic?”

“Wouldn’t know,” Jess deadpans. “Haven’t met them.”

Emily casts a disdainful glance over at Luke, who has begun to snore. “Probably not the biggest tragedy.”

“Not if they’re anything like my father,” Jess agrees.

Emily doesn’t reply; she’s seemingly drifted off into some sort of reverie.

“You okay?” Jess asks, eyebrow raised. “You look like you’ve just run into Casper.”

“Yes, yes, I’m fine. It’s just…” Emily furrows her brow, not meeting his eyes. “I haven’t been a huge fan of hospitals, not since…” She trails off and ducks her head.

Jess leans forward a bit, frowning. “Since Richard,” he finishes for her.

She nods. “I lost my husband only two years ago. I sat in chairs just like these in a room just like this, walked into a room just like the ones here, and watched him…” She swallows. “It’s silly, I know.”

“It’s not,” Jess assures her. 

Emily dismisses his statement with a wave of her hand, but she’s not altogether ungrateful. Jess offers her a tissue box, which she accepts. “I just wish he could’ve been here for this.”

Jess nods, not altogether sure how to respond. He maxed out on sentimentality about ten minutes ago.

“It’s an emotional day,” Jess offers.

Emily sits up, suddenly stiff again. “Is Logan coming?” Great. Back to our regularly scheduled programming.

“We called him, but he didn’t pick up.”

“So, that’s a no.”

Jess restrains himself from rolling his eyes. “As far as I’m concerned, yes, it’s a no.”

“Well, then.” Emily sits up a little straighter and folds her hands in her lap. Jess kind of resents Luke for sleeping through this - he could do with a little moral support. “Jess. You and Rory are...you’re living together, now, right?”

“Yeah.”

Emily hesitates. This conversation is _ agonizingly _slow. “And you’re still...raising the baby together.”

“Yes.” When Emily doesn’t reply, Jess sighs. “Look. I know I’m not Logan, but…” He pauses, thinking about what Luke said. “But I’m the one that’s here, okay? I’m going to be...I’m…” Jess takes a deep breath. “I’m going to be a good father.” Maybe if he says it enough, he’ll believe it.

Emily doesn’t look at him. “You have to understand, in my day, this wasn’t how things were done. You got married, had a kid, and stayed together. This isn’t-”

“I know,” Jess interrupts. Emily gapes at his nerve to cut her off. “But things are different now. And even if they weren’t…” He shakes his head. “This whole arrangement isn’t going to change.”

Emily stares down at her lap and doesn’t say anything for a while. When she speaks, her tone is suddenly quiet. “I used to think that Logan and Rory were meant to be. With our families getting along, the way they worked...I got used to the idea that they would get married and have kids and be happy, like Richard and I.” Pause. “I should’ve known that no one could be like Richard and I.

“I thought it was something so close to fate, you know, that their relationship could be so similar to what I had with my husband. I wanted her to be happy, and I thought that what Richard and I had was what you _ needed _ to be happy.” She pauses again. “But then, Lorelai and Luke, they’re not like that. They have their own thing, just like Richard and I.”

“You can’t quite have a love like that, either.”

“No, you can’t.” She sighs. “I know that Logan isn’t in the picture. I understand. I thought he would be, for a long time, but now, I understand. Even if I don’t like it, I understand.” She looks over at Jess. “Just don’t ever come home with a black eye.”

Jess cracks a smile. “I won’t.”

Slowly, Emily smiles back. 

**

Lane and Zach arrive soon with their two boys, whom Jess doesn’t know very well, but he has to admit, they’re cute. Sookie and Jackson run in not long after, looking a little hassled from the drive up. Jess says a polite hello to them, humoring Jackson by answering his vegetable riddle and debating with Lane over the latest Bowie album and how many more iterations of _Africa_ that the world can endure.

More people pour in, hassling the poor receptionist. Lorelai must have let many citizens of Stars Hollow know, because even Jess recognizes many of their faces; Babette and Maury, Miss Patty, and even Kirk. Michel is there, too, whom Jess narrowly avoids. Even Jess has to admit: it’s heartwarming, really, how many people are here to support Rory. He used to think that Stars Hollow was hell, but now, he guesses he could be persuaded otherwise.

Of course, he has to talk Paris down once she arrives. “I run a renowned fertility and surrogacy clinic, I must have _ some _ authority here,” she grumbles as Jess drags her away from the receptionist who’s probably considering quitting and becoming a lawyer.

“Calm down, she’s gonna be fine,” Jess snaps, forcing Paris to sit down with him. 

“I’m surprised you’re not pacing up and down the room like they would in the _ Mary Tyler Moore Show.” _

“Oh, I did that before you got here.”

“I’ve got some moonshine in my purse, if you need it,” Paris mutters to him, something that would absolutely make Rory say, _ Oh, my god! _

Jess snorts. “Do you really-” Paris reaches into her purse and shows him her flask. Jess shakes his head. “Classic Geller.”

Paris isn’t put off by his comment; she merely puts the flask back and sets her purse down by her feet. “Do you think it’s gonna be a boy or a girl?”

“Rory and I have a bet going. I say girl, she says boy.”

“What do you get if you win?”

Jess smirks.

“You’re disgusting, Mariano.”

“Not _ that! _ Jeez,” Jess says with a laugh, shaking his head. “No, if I win, she has to read _ The Old Man and the Sea.” _

“Classic Hemingway. And if she wins?”

Jess makes a face and shudders. “I have to read _ Atlas Shrugged.” _

Paris rolls her eyes. “Domesticity has officially rendered both of you _ boring.” _

Jess shoots her a look. “You here to do anything else than criticize our lifestyle?”

“Also, Ayn Rand isn’t that bad.”

“Of course _ you’d _ say that.”

Paris glares at him. Jess can’t help but laugh.

**

An hour or so later, a very tired, but seemingly still exuberant, Lorelai emerges. The air goes completely still as everyone in the room freezes.

“I was hoping for a standing ovation, but I suppose this will do,” she sighs dramatically. “Well, the show has to go on, right?”

“How’s Rory?” Babette calls out. “Is it a boy or a girl?”

“Figured you’d all want to hear about that.” Lorelai grins. “I’m happy to report that everyone is alive, well, and functional. She’s very tired, but good. And it is with great pleasure that I announce that Rory Gilmore has just given birth to a happy, healthy baby boy!”

The room erupts in applause; the receptionist shoots them a look, but no one pays any mind. “Encore!” Jess calls out, as a joke, but he could not be smiling any wider.  
(Well, maybe he _ could, _ without his crooked mouth and all, but Rory really likes it, so there really isn’t any problem.)

“When can we see Rory?” Miss Patty asks. 

“She’s just resting, but we’ll be able to go in soon, once they move her to a postpartum room,” Lorelai says, to Jess more than anyone else. 

He gives her a nod. Lorelai smiles, and everyone quiets down, waiting. “Oh, uh, class dismissed,” she jokes, and the hush is lifted. She walks over to Jess.

“Hey, kid, you think we can talk for a minute?”

“Sure, why not?”

He follows her over to the coffee machine. “On brand,” he comments.

She offers him a smile. “Yeah, well, it has been a _ long _ few hours.”

“I’m sure Rory would agree.”

“Oh, trust me, she probably fell asleep the second I left.” Lorelai finishes making her coffee and takes a sip. “Alright, let’s sit down. I’ve been on my feet for _ way _too long.”

“What did you have to talk to me about?” Jess asks, crossing one leg over the other. 

Lorelai takes another sip. “Have you ever thought about getting your GED?” She asks, right off the bat.

Jess’ brow furrows. “What?”

“It’s not that hard, really, just a few classes and then the test. I did when Rory was younger, and ended up going to a community college up in Hartford.”

Jess nods; he has a vague memory of Rory mentioning something like this when she visited him in New York all those years ago. “What’s your point?” He asks, a little on edge.

Lorelai sighs. “I was just wondering. It can help, you know, in the long run-”

“What, so I can better provide for your daughter?” He asks sarcastically, his tone bitter. “Sorry, didn’t see you as the _ Picket Fences _type.”

“Hey, Jess?”

He raises his eyebrows.

“This whole ‘you’re not as good as Dean’ shtick? It’s in the past,” Lorelai says firmly. “Rory chose you. Chose you twice, actually. I think that’s a pretty good reflection on you, but hey what do I know?”

Jess stares down at his lap, silent.

Lorelai sighs. “Look. I know there’s always going to be a level of insecurity when it comes to this. Lord knows none of us helped back then. And this kind of thing, it doesn’t go away easily, but you gotta trust me on this one, kid. You’re exactly the right person for Rory.”

Jess blinks a few times and takes a shaky breath. “I am, huh?”

Lorelai smiles. “I know that I wasn’t patient the first time. And I’m sorry for that. You...you scared me a bit, I think. Reminded me a little too much of myself.” She sighs. “You’ve matured a lot, Jess, more than I ever could. You’re reliable, successful...I guess I was just wondering. A GED can be a good thing to have, just in case you ever want to pursue more education.”

“I get it.” Jess bites his lip. “I’m happy at Truncheon. And if I have to spend another minute in a class I’ll lose my shit.”

“You better watch that mouth around the kid,” Lorelai quips. “But, that’s good. I just wanted to bring it up.”

Jess smiles. “Thank you. You know, for…” He trails off.

“Anytime.” Lorelai stands up and stretches a bit before cracking a grin. “You ready to see your kid?”

  
  


**Notes for the Chapter:**

> Two! More! Chapters!


	29. Places We Were Made

**Summary for the Chapter:**

> Jess and Rory name the baby.

**Notes for the Chapter:**

> This ones kinda lame and short but it’s more or less a filler also I literally could not be bothered to edit this more so it could very possibly be bad

“Rory?”

Rory glances up. “Hey,” she murmurs with a tired smile.

Jess smiles and closes the door quietly behind him. “How’re you feeling?”

“Good,” she replies immediately. “Tired, but good.”

He pulls up a chair next to her bed and sits down. “I’m proud of you,” he murmurs.

Rory flushes. “I love you.”

“I love you, too.”

They sit in comfortable silence for a moment before Jess clears his throat. “I, uh, I had a talk with your grandmother earlier.”

“Oh, no. What did she say to you? I swear, if I have to yell at her, I’ll-”

“Ror, Ror, it’s fine,” Jess says, laughing. “It wasn’t bad. It was...interesting.”

Rory frowns. “What do you mean by that exactly?”

“It was as close to an apology that one can get from her, I think,” Jess replies with a shrug. “But I don’t think we’ll be going out to dinner together any time soon.”

“There’s always time for that,” she reminds him.

Jess smiles. “That there is.” He pauses for a moment before he speaks again. “So, a boy,” he breathes, unable to hide his smile.

“Yep. That means you lose, Mariano. Pay up.”

“God, I can’t believe I have to read _ Ayn Rand _ now.” Jess groans. “You suck.”

“Hey, I just pushed a human being out of my body,” Rory reprimands him. “You can deal with a few forty-page monologues.”

“I suppose.”

“Besides,” Rory continues, “I’m not offering we name him Dagny or Ragnar.”

Jess grimaces. “A hard no to both of those.”

Rory smiles softly. She glances down at the bundle in her arms and then back at Jess. “Want to hold him?” She asks.

“You sure?” Jess looks wary. 

Rory laughs at the look on his face. “C’mon, he’s not gonna break. Here.”

She’s a natural, moving Jess’ hand under the baby’s head, handing off the newborn gently and carefully. She watches as Jess supports the weight on his own, as the expression on his face slowly changes. 

(She can barely contain her own grin, watching him, biting down hard on her lip.)

“You can’t read him Kerouac until he’s at _ least _fifteen.”

Jess laughs quietly. “What about Ginsburg?”

Rory scrunches up her face. “He’s even more explicit. Sixteen.”

“I was only fourteen.”

“I doubt Liz knew exactly what was in that book. Couldn’t exactly warn you not to read it.”

Jess snorts. “I believe the only book I remember her reading was _ Goodnight, Moon. _After that she kinda gave up.”

It’s quiet for a moment, Rory shifting a bit at his words. “But,” he continues, “Howl was essential to our early romance. You can’t keep that from him.”

Rory rolls her eyes, but she’s smiling. “We’ll talk about this later.”

“You got a name?” Jess asks after a pause. 

“Yes, I am Jim Croce,” she jokes. “I thought everyone just assumed, well…” Rory shifts a bit. “That…”

Jess nods in understanding. “Is that what you want?”

Rory nods. “Yeah. It is.” 

“Okay,” Jess says softly. 

“What about you?” She asks. “Do you like it?”

“It hardly matters what I think. It’s up to you.”

“Oh, shut up. You _ know _ you get just as much a say in this as I do.” 

Jess looks down at the baby he’s holding, and there’s an odd twinge in his heart - but it’s not unpleasant at all. “Yeah. I like it.” He looks up at her. “I like it a lot, actually.”

Rory smiles wide and doesn’t say a word. (She doesn’t really need to, anyway.)

**

“Much to Babette’s dismay, they’re only letting family in,” Lorelai explains as Emily, Jess, Lane, and Paris. “I had to slip them a crisp twenty to let in Paris, and I told them Lane was a fifth cousin twice removed. Adopted, of course.”

“Oh, my god!” Rory says, at the same time that Emily exclaims, “Lorelai!”

Jess eyes them amusedly. “How much bribing did it take to get me in?”

“Oh, did I forget to mention that you have to spend a night with the receptionist?”

“Lorelai, seriously!” Emily chastises. “I can’t _ believe _ you would say that-”

“What, like the infant in the room will hear me and suddenly decide to lead a life of debauchery and crime?”  
“It’s still not appropriate-”

“Okay!” Lane interrupts, clapping her hands. “I think we all want to hear what they named the baby, right?”

“Some of us have places to be,” Paris adds sharply.

“Paris, go get a drink,” Jess says, rolling his eyes. “Or did you forget the liquid courage you have stashed in your purse?”

“Oh, my god!” Rory says again. 

Lane clears her throat. “Anyway!”

Rory looks down at her son for a moment with a big smile she can’t contain no matter how hard she tries. (She’s not trying at all.) “So, Jess and I have decided that this little guy right here will from here on be known as Richard Gilmore-Mariano.”

“The second,” Jess supplies.

“No, that’s only if he was being named after his father.”

“And it would be Richard junior, anyway,” Paris adds.

“Technicalities.”

Rory sneaks a glance at Emily and Lorelai, her heart skipping a beat at the looks on their faces. “You like it?” She asks softly.

Lorelai’s eyes are shining a bit more than usual. “Yeah. Yeah, I do.” She clears her throat.

“Aw, don’t get soft on me now, Lorelai,” Jess groans. 

Lorelai laughs. “I’m afraid to say I’m not living up to my reputation as a stone cold-“

“_ Lorelai,” _ Emily reprimands, but her tone lacks any sort of real malice. 

“Grandma?” Rory asks.

Emily shakes her head, not to say no, unable to not smile. “He would’ve loved him,” she says simply.

Not even Jess can be emotionless after that. 

**

Soon enough, their things are backed, the carrier brought over from their apartment, and it’s time to go

home. 

Jess triple checks that Richard (Ricky, as Lorelai has dubbed him), is secure in his carrier as Rory goes through the diaper bag, making sure she has everything.

“Blankets?”

“Mhm.”

“Clothes?”

“Yep.”

Jess looks up from the carrier. “I think we’re good on the supplies, Ror.”

“Shouldn’t we triple check?”

“If that’ll help you sleep at night.”

“You better be prepared not to get _ any _ sleep for a while,” Rory says, zipping up the bag. “Not for a few weeks. Or months. Maybe years.” She catches Jess’ smirk and rolls her eyes. “Not like _ that.” _

He laughs. “No?”

“You’re on thin ice, Mariano.”

Jess surprises her with a quick kiss on the cheek before picking up the carrier and Rory’s bag. “I can take-“ she starts, but Jess shakes his head.

“Not a chance.”

“But-“

“Nope.”

She smiles gratefully. “You ready to go, then?”

“I’d say so.”

She looks down at Ricky before looking back at Jess. “Alright,” she says. “Let’s go home.”


	30. Epilogue

**Summary for the Chapter:**

> Three years later, Jess and Rory have decisions to make.

**Notes for the Chapter:**

> So, here we are. The last chapter. I just want to start this by saying thank you to everyone who read, commented, gave kudos, and generally supported me and/or this fic. It was my first chapter fic, and I definitely learned a lot from writing it. I love you all and I hope you enjoy this final chapter.

“Have you talked to Jess about it yet?”

Rory stops her pacing abruptly and stares at her mother incredulously. “Have I talked to Jess about it yet? Have I - do you think I would be freaking out about this right now if I had?”

“Well…”

_ “Mom_,” Rory groans. 

“Well, you asked!”

“I don’t know what to do,” Rory admits. “We haven’t...we haven’t talked about this yet.”

Lorelai nods in understanding. “Well, you can only know how he’ll react if you tell him. Why haven’t you?” She asks after a pause. “I would’ve figured that you - Rory Gilmore, the girl who has a plan for everything - would’ve brought it up the second you moved in together.”

Rory can’t quite meet her mother’s eyes. “It just...it never came up.”

Lorelai sighs. “Rory, honey, maybe you’re just...scared.”

“Of course I’m scared!” Rory exclaims. “Of course I am. I just...it didn’t go great the last time this happened, and I…”

“Yeah, but this is _ Jess, _not Logan,” Lorelai points out. “The two are not the same. Not in the slightest.”

“What would you even want me to say? ‘Hey, honey, I’m home! By the way, I might be pregnant! What do you want for dinner?’”

“Isn’t Jess the one who does the cooking?”

“Mom, focus!”

“Right, right.” Lorelai frowns. “How are you two even still have time for this? You’re still having sex?”

Rory flushes pink. “What’s that supposed to mean?”

“I just mean, you have a two year old running around. You still have the energy and the time?”

“That isn’t the point,” Rory says hurriedly. “The _ point _ is that my period is late, and we haven’t even _ discussed _ the possibility of having any kids together. We’ve been happy the way things are, and this would just confuse everything.”

Lorelai softens at that. “I get it. I do,” she emphasizes at Rory’s skeptical look, “but you gotta face the music, kid. If you are pregnant, which you might not be, it’s gonna have to come up eventually.”

“I know.” Rory sighs. “I just...don’t want things to change.”

“I know,” Lorelai says reassuringly. “But I have a feeling that if you are pregnant, or it happens down the road, it’ll make things even better.”

“How can you be sure?” Rory implores. “When we don’t even know how he’ll react?”

“There’s only one way to find out.”

“Yeah,” Rory breathes out. 

“Not to mention,” Lorelai adds, “look at how he is with Ricky. You really couldn’t be in this situation with anyone better suited for it, could you?”

Rory’s heart does a little flip at that. “No, I couldn’t.”

“Then it’s settled. Tell him as soon as you can. And besides,” Lorelai continues when she sees Rory about to interrupt, “you don’t even have to have the baby if you don’t want to. You can always exercise your right to choose, you know.”

“I don’t even know what I want,” Rory says. “Or what I’m ready for.”

“I know, honey.”

“Can I at least take a test before I talk to him about it?” Rory asks weakly. “I’d rather know for sure before we start having a real conversation about it.”

Lorelai smiles. “Of course you can. This is all up to you.”

“Really? I had the distinct feeling someone else was in charge about two minutes ago when you started getting on me to tell him.”

“Come on, we can drive up to Woodbridge so the news of you buying a _ pregnancy test _doesn’t spread like wildfire around here.”

Rory grins; she can feel herself start to relax. “Okay.”

Just then, the front door opens, and familiar footsteps sound down the hall. Jess pokes his head into the living room and grins when he sees Rory. “Hey. You about ready to go back home?” 

Rory nods. “My mom and I have a few errands to run first, but then I’ll be ready to go.”

“Good.” He nods at Lorelai. “Everything’s all good on the home front?”

“Yeah. I’m still trying to convince Luke to let me get a new dog, though.”

Jess snorts. “Good luck with that.”

“Hey, I’m making some progress,” Lorelai argues. “I think all the hints I’m dropping are really working their way into his subconscious.”

“And what are those hints, leaving pictures of dogs all around the house? Or, even better, making about ten dog-related puns a day?”

“It could work.”

Jess scoffs, but he’s still smiling. “Yeah, well, I’ll make sure to leave a picture of an akita in his baseball hat next time I’m here.”

“Would you? I need to fill that Paul Anka-sized hole in my heart.”

Jess gives Rory a quick kiss. “Let me know when your errands are all wrapped up, okay?”

“And where will you be?” Rory asks, grinning.

“Diner.”

“Got it.” She takes the collar of his jacket in her hands and kisses him. “I’ll see you later.”

He steals another kiss before he leaves. The front door shuts, and Rory reluctantly turns to face her mother again. 

“Aw, that was totes adorbs!”

Rory rolls her eyes. “I appreciate that you’re trying to make up for your attitude about Jess and I the first time around, but you’ve been going a little overboard, don’t you think?”

“I don’t know what you’re talking about,” Lorelai replies matter-of-factly. 

“Mhm. Sure.”

“Let’s get going, shall we?” Lorelai hops up from her perch on the top of the couch and grins. “Gotta find out if there’s a bun in that oven!”

“Quiet- Babette might be able to hear you!”

**

“So, two lines if you’re pregnant, one if you’re not,” Lorelai says, reading off the back of the box. “Take the sample for at least seven to ten seconds. Point the absorbent tip- God, this is disgusting.”

“You know I’ve taken one of these before, right? And so have you,” Rory reminds her, shutting the bathroom door and locking it for good measure. “It’s not like this is news or anything.”

Lorelai sighs dramatically. “I’m well aware. Got the stretch marks to prove it.”

“Alright, so, let’s get this over with. Rip off the band-aid,” Rory says, a little agitated. 

Lorelai hands her the box. “You’ve got this,” she says firmly. “It’s gonna be fine. You know that, right?”

Rory nods, but her heart isn’t in it. “Yeah. Yeah, I do.” She holds the box and stares down it, feeling a familiar sense of anticipation. 

“Whatcha thinking about?” Lorelai asks, catching the uneasiness in Rory’s expression.

Rory swallows and tears her eyes from the box. “Nothing. Just...am I ready? If it’s positive? We haven’t been saving or anything, and-”

“Just take the test. Then we’ll go from there.”

Rory bites her lip. “Okay. Okay, yeah, I will.”

“And Rory?”

“Hm?”

Lorelai smiles. “You’re already a great mom.”

“Well, I learned from the best.” Rory kisses her mother on the cheek. “Okay. Get out of here so I can pee.”

**

Negative. For all the wishing and hoping she’s done for the past five minutes, there’s an odd dropping sensation in her gut that she refuses to acknowledge as disappointment. It’s negative. 

“This is good, right? This is what you wanted?” Lorelai checks, frowning at the look on her daughter’s face. 

Rory swallows and nods. “Yeah. Yeah, no, this is good. Makes it a lot easier to talk to him, right?”

She’s trying to convince herself, and Lorelai knows - but her mother just smiles. “Let me know how it goes, okay?”

Rory smiles weakly. “I will. Don’t worry.”

“I could say the same to you,” Lorelai quips, rubbing Rory’s arm reassuringly. “You’ve got this,” she says for the second time that day. “Don’t forget that.”

Rory squeezes her eyes shut and nods. She really, really hopes that it’s true.

**

Jess is already in bed and reading by the time Rory finishes putting Ricky to bed for the night and getting ready for bed. She stands by the bathroom door for a moment and takes a deep breath, willing the anxiety to go away. 

“Jess?” She asks, sitting down on her side of the bed.

He glances up from his book - _ Mother Night, _ a reread - and offers her a smile. “Yeah?”

“We need to talk.” 

His brow furrows in concern. “What’s up?”

Rory swallows and fights the urge to stare down at her lap. “So, for the past couple days, I thought I might be pregnant. I’m not - I took a test today, that was the errand I had to do with my mom - plus, I got my period, but it made me realize that we need to talk about the future and what we want to do. You know, kid wise.”

Jess nods slowly. “Are you okay? How do you feel?”

“Yeah,” Rory says with a smile. “I’m...I’m good. If I’m being honest, though…” She trails off.

Jess frowns. “What is it?”

“If I’m being honest - really, really honest - I think I was a little disappointed that I wasn’t,” Rory admits. “Pregnant, I mean. But I don’t know. It all happened really fast, and we haven’t even talked about it.”

“You like to be prepared. It’s totally understandable.”

“But...what about you?” Rory asks nervously. “Like, if I got pregnant for real, how would you feel about it?”

“I think I’d be happy,” Jess says after a thoughtful pause. “I do. I mean, I love Ricky, and what we have now, but having a kid with you would be…” He smiles. “It would be really cool.”

Rory blushes - it’s funny how after all this time he still has this power over her. “So, what now?”

Jess clears his throat. “Do you...do you want to try?” 

“I don’t know if I’m ready right now,” Rory admits. “Soon, definitely, but...what if we’re not ready?” She asks anxiously. 

Jess shrugs. “I don’t know if the timing will ever be perfect. This is the kind of thing we go into together, being ready to face any challenges that might come up, right?”

“Definitely,” Rory agrees. “I just want to make sure that we’re in a good place. Financially, mostly.”

“My book is publishing in a couple weeks,” Jess reminds her, “and we’ve got both of our jobs to rely on. Once sales start coming in I think we’ll be fine.”

“I _ still _ can’t believe you won’t let me read your book.”

“You’ll read it when it releases like everyone else.”

“I’m your _ girlfriend,” _ Rory huffs. “I should get to see a sneak peak at _ least.” _

“Keep this up and I’m demoting you to roommate.”

“Oh, please, you wouldn’t last a week without being able to be with me every night.”

Jess smirks. “Someone thinks highly of themselves.”

Rory sticks her tongue out at him. “You owe me.”

“I’ll keep that in mind.”

“Do you really think we’re ready?” Rory asks. “Can we handle two kids?”

“We can do anything, can’t we?” Jess smiles. “Consider everything that’s been thrown at us. We’ve come this far, haven’t we?”

“I guess so.” Rory hesitates before continuing. “So, is this it? Are we deciding to try for another kid?”

The way he looks at her really shouldn’t still make her heart skip a beat, but it does. “Yeah, I think we are.”

Rory can’t help but grin. “We’re doing this.”

“We’re doing this.”  
Rory cups his face in her hands and kisses him. He kisses back, softly, tenderly, before pulling back and resting his forehead against hers. “I love you. You know that, right, Gilmore?”

She smiles. “I think you’ve mentioned it once or twice.”

“Just making sure,” he murmurs before kissing her again.

When she pulls back, she’s just a little breathless, and the look in his eyes _ really _ makes her wish it wasn’t that time of the month.

“We can practice,” Jess offers, as if reading her mind. “Make sure we’ve _ really _ got this thing down.”

Rory rolls her eyes. “Slow your roll, Mariano. May I remind you I’m on my period?”

Jess just quirks up an eyebrow and grins mischievously in response. 

“Jess!” Rory squawks, shaking her head. “Absolutely not.”

“Fine, fine.”

“What was that about demoting me to roommate, again? I’d like to reconsider.”

“You love me.”

“And you bug me.”

Jess kisses her again before pulling back and laying his head on her lap. “What’re you reading?”

_ “The Glass Castle.” _

Jess closes his eyes and smiles. “Read it to me.”

**

The night before Jess’ book is set to release, he and Rory drive to Stars Hollow for dinner with Luke and Lorelai. It’s a nice evening, really, and while Lorelai plays with Ricky after they eat, Jess grabs something from his bag and asks Rory if she’d like to take a walk. 

“Sure,” she says with a grin. “Just let me grab my jacket.”

_ “Jess Mariano’s triumphant return to writing - _Jess, this review is incredible!” Rory exclaims, reading off her phone as they head towards the bridge. “But I still can’t believe that the reviewers got to see it before me.”

Jess smiles at her and shakes his head. “You’re never gonna let that go, are you?”

“Depends on how forgiving I’m feeling after I read it.”

“You were the muse,” Jess reminds her. “I’d be disappointed if it didn’t put you in a forgiving mood.”

“Yeah, yeah.”

Jess doesn’t sit down right away when they reach the bridge. He looks out on the water, his expression unreadable.

“This place has a lot of memories, doesn’t it?” He asks, eyes still fixed on the water. 

Rory smiles. “It’s more or less ours now, I think.”

He fiddles with his hand inside his pocket. “It’s my favorite place in this town.”

“Well, it has to be, considering this is where it all started.”

Jess returns the smile. “I actually wanted to give you something,” he says after a pause. He reaches into his jacket pocket and hands her something - a book. _ His _book.

Rory takes it from him and stares down at the cover in awe. “I figured I’d let you see it tonight,” he explains, “before everyone else. The least I could do after making you wait for, what, three years?”

“I’m so proud of you,” Rory gushes, unable to tear her eyes from the book. “Thank you. So much.”

Jess smiles. “Why don’t you open it up?”

Rory opens up the front over, relishing in the feel of a book unread and untouched. She flips to the next page - title page - and grins at his work, his title, in print. 

“Check out the dedication,” he offers, a tiny bit of an edge to his voice. 

She starts to read it out loud. “To Rory - I love you. Will you-“ Her heart stops in her chest. Time stops completely. “Will you marry me?” Her voice is barely a whisper.

She slowly turns around, not exactly afraid, but her heart still feels frozen in her chest and she’s completely out of breath. “Jess.” 

“I’ve been thinking about this for a while,” he says softly. “And I wasn’t sure if - if it was the right time, but what I do know is that I love you. And I have for a really, really long time.”

She can’t even look at the ring; she can only look at him. 

“So here we are, on this bridge, and I - I want to spend the rest of my life with you,” Jess chokes out, his smile uncharacteristically wide. “If that’s okay with you.”

Rory grins. Her eyes are wet, but she can’t be bothered to wipe them. “Yeah. Yeah, it’s okay.”

“You are the only girl I have ever loved, and I never thought - I never thought we’d get another shot. That _ I’d _ get another shot. But we did, and we are here, and I have never been happier.”

Rory’s heart skips a beat. “I love you so much.”

Jess smiles - that same, crooked relaxing, familiar, making you fall head over heels, causing your heart to stutter and skip six beats at one smile. “I’m gonna do this now, okay?”

She nods.

He takes a deep breath. “Rory Gilmore, will you marry me?”

She smiles, her heart beating a mile a minute, and she loves him _ so _much. “Jess Mariano, I will marry you.”

Jess lets out a sigh of relief, all the tension leaving his body as he gets up and puts the ring on her finger. She kisses him, hands on either side of his face, still unable to stop from smiling when she pulls back. 

“I love you,” she breathes.

“I love you, too.”

She can’t help but kiss him again. 

  
  


**Notes for the Chapter:**

> Until the next time.


End file.
